Lipstick & Miniskirts

by John Dylena

  The long brown hair of his wig fell down past his shoulders where his black lace bra was clamped tight across his back. The cups were stuffed with tan socks, as he had yet to purchase a pair of falsies. His acrylic nails, colored the same as his lipstick, tapped softly against the underside of the sink, the noise fading before it even reached the door.

  He leaned forward and looked down past his flat tummy to his feet. The fear and anxiety that now coursed through his veins caused his dick to shrivel, almost retreating entirely into his body. The bulge on his matching black lace panties was barely noticeable.

  His legs were encased in sheer black stockings held up by a matching garter belt that clung to his hips. The hair on his body was gone. Josh had waited maybe ten minutes after Will and Nicole had left to step into the shower and shave.

  It wasn’t the first time he had done it. Shortly after the first time Josh decided to completely shave, Will had taken notice. When confronted about it, Josh had simply said that he’d done it to cut down on his body odor. Will had just shrugged his shoulders and never mentioned it again.

  On his feet were a pair of black pumps; his pride and joy. They were the first pair of women’s shoes he owned, now one of four. His current collection included a pair of high-heeled boots, red Mary Janes, and a pair of six inch, clear-soled, platform hooker heels. That pair he’d bought to go with the miniskirt and the tube-top that would’ve barely covered a large breasted woman. He was saving that outfit for when the falsies came.

  Five inches of shiny black patent—he couldn’t help but smile at how smooth and polished they still were. There was barely a scuff on them, despite how many times he’d worn them.

  Joshua had crossdressed before in the apartment he shared with Will: the nights when he would go out drinking and stay at Nicole’s; the short weekend business trips his work assigned to him. Most of the time, Joshua would just put on a couple items of clothing. It was on the weekends he had to himself that he indulged in full blown, head-to-toe transformations.

  This weekend was going to be a special one. Hanging up in his closet, tucked away behind several large rain jackets, was a bright red dress. A short dress, it was designed to be worn to clubs or anytime a woman wanted to get plenty of attention from the men.

  Not only that, but still in the box that it had been shipped in was a dildo. The skin-colored phallus had a suction cup on one end, and Josh had planned on using it some time that night after he’d emptied the bottle of whiskey he had purchased earlier in the day. After weeks of going back and forth in his mind, he had finally committed to it, and clicking the ‘submit order’ button on the website was one of the hardest things he had ever done.

  “Josh?” Will’s voice was softer.

  “He’s probably out getting dinner,” he heard Nicole say. The blonde bombshell was always nice to him, and more than once Josh wished she was his girlfriend instead of Will’s. Not that Will was a jerk or anything, but it was hard to compete with a man that was as naturally good-looking as Will. Short black hair; strong features; great body; he was a chick magnet.

  “I’ll call his cell. Maybe he can pick something up for us.” Josh bit his hand. His cell phone was on his desk in his room and it wasn’t on vibrate.

  “No, wait. Let’s not give him a reason to hurry home,” Nicole said rather impishly.

  “Clever girl.”

  Josh could hear the sounds of their kissing through the walls of the bathroom. Since they believed that they were alone, there was no reason to limit the volume of their cries and moans.

  Josh rubbed his face as he listened to the sounds of them making love. Their footsteps were heavy, and in between the giggles and moans were the sounds of them moving around the apartment.

  Come on Will, take her to your room and close the door! Josh moved a strand of hair behind his ear and waited, listening intently. The moment he heard the sound of Will’s door closing, he would bolt from the bathroom to his own bedroom across the hall.

  Will and Nicole’s lovemaking grew louder and louder. He held his breath and closed his eyes, silently praying.

  The doorknob turned and Josh’s heart stopped.

  “What the fuck?”

  Josh turned sharply on his heels and faced the two of them. Will and Nicole stood in the bathroom doorway and Josh, no more than six feet away, stared back. In their lovemaking fury, Will had blindly reached for any knob, as any room in the apartment would’ve been good for the sex he was about to have. Nicole slid out of Will’s arms and pulled her top back down over her body.

  Josh could feel the blood flow to his face as his stomach twisted into the mother of all knots. “Hi, Will,” was all he could say. His mouth was dry, his body shook nervously, and his heart pounded in his chest.

  “Josh? Is that you?”

  “Yeah, it’s me.”

  “Holy crap… I mean… dude, you’re dressed like a chick! Are you a homo?”

  Nicole punched him on the arm. “Will!”

  “Ow,” he said rubbing his bicep. “But seriously, are you like, gay?”

  “Goddamn it, Will!” Nicole pushed him out of the doorway back into the hall. “Hang on a sec, Josh,” she said to him before closing the door.

  “Heh, sure. Not like I can go anywhere.” His voice was quiet, meek, and ultimately lost in the shouting match going on between the couple in the hallway. Josh turned away from the door and leaned back over the sink. His stomach was so tightly wound it was about ready to tear.

  Are you a homo? Will’s blunt question hit him hard. It was something he never thought he would have to explain to someone. He was in a situation he never thought he’d be in. No one with such a taboo hobby wanted to be caught, even if they knew that the people that saw them were open and accepting.

  Yet deep down, lingering beneath the fear and the anguish, something stirred inside of Josh. There was a warmth nestled in his groin; a soft, euphoric sensation and it stood idly by, biding its time.

  He lifted his head up and stared at himself in the mirror, fear and panic all over his face when he realized that underneath it all, he was incredibly aroused.

  The more he thought about it, the more he realized that his sexuality wasn’t set in stone and more often than he’d like to admit, he found himself lingering on the pictures of the men with big dicks penetrating the sexy and slutty women of porn.

  Will and Nicole’s argument subsided, and hearing the knob turn once more, he turned to face the couple.

  Will stepped into the bathroom, his head hung low. Nicole stood behind him, her hands on her hips. Her pose was motherly, as if Will was her child that she just disciplined and forced to apologize to the person he wronged.

  “Josh, I’m sorry for being so blunt, but—”

  “It’s fine, Will. How else were you supposed to react to seeing me dressed like this?”

  “Yeah, about that,” Will averted his eyes away from Josh, as seeing his roommate dressed in sexy lingerie and looking rather convincing made him feel uncomfortable. “Sorry if I offended you.”

  He barely finished the sentence before he turned and walked out of the bathroom. It was at that moment that Josh’s eyes lowered and spotted the bulge in the front of Will’s jeans. He turned back to the sink and bit into his hand. His outfit had aroused Will.

  Josh’s roommate slid by Nicole. The blonde with wavy hair and ocean blue eyes sighed and faced Josh. She took a couple steps into the bathroom and closed the door behind her.

  Josh looked at her through the reflection in the mirror. Nicole moved slowly toward him, her arms crossed in front of her with a faint smile on her lips.

  He had seen this before. Two months ago, both of Will and Nicole came back to the apartment plastered. Will collapsed onto the couch and when Josh came out of his room to see what was going on, he spotted Nicole walking toward the bathroom. She wore a tight blue dress with matching blue pumps. Her hair was disheveled and one of the straps of her dress had fallen off of her shoulder. The other just bar
ely held on.

  She noticed him standing in the hallway outside of his room. Will was snoring on the couch and she lingered, her eyes all over Josh. She was a lioness, and he was her prey.

  Nicole had moved away from the bathroom and took a step forward toward Josh. He was a shy and socially awkward man, and seeing a woman as beautiful as Nicole moving toward him with such a hungry look in her eye had scared him.

  He’d known right then and there that if it hadn’t been for the sudden onset of nausea, she would’ve been all over him. Nicole had looked away from him and disappeared into the bathroom, and he had taken the opportunity to return to the safety of his room.

  Neither of them remembered coming home that night. If Nicole did remember coming onto Josh, she kept it to herself.

  “You know Josh, you look pretty good. Your makeup could use some adjustment, though.” She took another step forward and he faced her. He was nervous, anxious, nauseous, and aroused all at once.

  “Thanks?”

  She took another step toward him, still outside arm’s reach, but she was getting closer. “If you ever need to talk, you can talk to me.”

  “I appreciate the offer, Nicole.”

  She bit her lip and looked down at the tiled floor of the bathroom. “I’ve never told this to Will, but I’ve always wanted to dress him up like a girl. I have a lesbian fantasy, and because I don’t want to cheat on my boyfriend with a woman, I made some adjustments.”

  Nicole took another step forward, pressing his ass against the smooth surface of the sink. There was nowhere for him to go.

  His heart raced in his chest as he tried to look away from her. This beautiful woman that he’d been secretly lusting after for so long had just opened up to him.

  “I… uh…” Words failed him as his body twisted and turned. In his lace panties, his dick came out of hiding. Josh was back in high school and the hottest girl in the entire school was talking to him. His eyes flicked every which way as sweat beaded on his brow.

  His throat clenched up and his mouth suddenly felt like it was filled with cotton balls. The world started to spin and he was on the verge of collapsing.

  Then her lips touched his, and everything stopped. The panic and fear, the confusion and anxiety; it all disappeared in an instant. The kiss was slow and passionate. There wasn’t a hint of alcohol on her breath.

  Josh leaned back over the sink, trying to pull away from Nicole. Even though he wanted so badly to kiss those soft, supple lips of hers, he couldn’t let her cheat on Will. But try as he might, Nicole continued the assault on his lips.

  She leaned forward, her perky breasts pressing against his chest and her hands on his hips. He could feel her thumbs slide under the band of his panties and start to pull them down.

  Josh took his hands off of the sink and put them on her shoulders. He pushed her off of him and their lips separated, a small string of saliva connected the two.

  “Don’t tell me you’ve never wanted to kiss me,” she said. “I’ve seen how you look at me.”

  “I… but Will…”

  “Yeah, what about me?” Nicole looked back over her shoulder at the doorway where Will stood, his arms crossed over his chest. He looked pissed.

  “Babe…” she began.

  “No, Nicole. What the fuck are you doing kissing him? I’m your boyfriend!”

  Nicole bit her lip. “Will, you know how you’ve always wanted a threesome?”

  “Yeah?” He raised an eyebrow and uncrossed his arms.

  “Well,” she continued, wrapping her arm around Josh, “how about it? You, me and Joslyn.”

  “Who the hell is Jos—oh…” Will stared at Josh and Josh looked back and forth between him and Nicole. She looked at him and smirked.

  “What?! No, no, no, no, no, no!” Josh slid out from under Nicole’s arm and moved into the corner of the bathroom.

  “Come on, Joslyn, it’ll be fun!” Nicole said, putting her hands on her hips and pouting.

  “Will you stop calling me that! I… I’m not… no!”

  “Yeah, Nicole… that’s kinda weird. I don’t want to plough my roommate.”

  “Yes, could we please stop talking about this?” Josh waved his hands in the air.

  “Will, could you please step out and give me a minute with Josh?”

  Will narrowed his eyes. “Okay, sure. But I won’t do it unless Josh tells me himself.” He stepped out of the bathroom into the hallway and closed the door. “And no kissing!”

  With the door shut, Nicole turned her attention to Josh.

  “No, Nicole. I don’t want to.”

  “Josh, you can’t honestly tell me that you haven’t thought about it.”

  “I…” Josh turned his back to Nicole. She was right—he had thought about it, and not just once. But it was never with Will. Whenever those thoughts slipped into his head, it was always with some non-descript, generic male. How could he say that he’d never thought about sucking another man’s cock or having one penetrate him when there was a dildo sitting on the desk in his room?

  She placed her hands on his shoulders and gently rubbed them. “Look, Josh, I’m not forcing you to do anything here. And just like Will, I won’t go through with it unless you want to. But let me just say this—from my experience as a woman, being with a man is wonderful, and in my honest opinion, every man should experience anal and the taste of a meaty cock in their mouth.”

  “Nicole…”

  “And Will is a very thoughtful and courteous lover. I’ll tell you what, if you go through with this, I’ll give you the best damn blowjob you’ll ever have. Maybe even something a little more, if Will lets me.”

  Josh bit his lip as his dick swelled in his panties. The thought of Nicole pleasuring him like that was too much. Countless times he’s jacked off to her, and with the possibility of that fantasy becoming a reality, it would be a mistake to pass up on it.

  He moved away from her tender touch and turned toward her. “It would be a lie for me to say that I’ve never thought about it. But I do emphasize the fact that I am only satisfying a curiosity.”

  “I understand, Josh.”

  He sighed. “I guess if I have to have sex with another man, having that man be someone I know and trust is the best option.”

  “But it won’t be just the two of you. I’ll be there as well. So, is that a yes?”

  Josh hesitated. He looked away from the growing smile on Nicole’s face to the door and around the bathroom. “Yes, I will go along with it. But this never leaves the apartment!”

  “I swear that this will stay a secret between the three of us. You won’t regret this, Joslyn!”

  “Do you really have to call me that?”

  “Is there another female name that you go by when you’re dressed like that?”

  “…no…”

  “Then, since tonight you are batting for my team, you can’t be a woman named ‘Josh.’ You gotta have a girl’s name.”

  “But Joslyn?”

  “It’s cute! And it rolls off the tongue.” She giggled to herself as she ran out of the bathroom. Josh sighed once more and staggered over to the sink and looked at his reflection in the mirror.

  “Well, now you can say that you’ve tried it. And if I don’t like it, then I don’t like it,” he said to himself. “But what happens if I do like it?”

  He remembered an old saying: I’ll cross that bridge when I come to it.

  Josh pulled himself away from the sink and walked up to the bathroom door. He reached for the door handle and his eyes dropped to his fingers. They twitched nervously as he gripped the knob. Hearing the front door of the apartment open and close, Josh stepped out of the bathroom into the hallway.

  “Will?”

  “Couch,” he heard his roommate say. Josh walked down the hallway into the living room, where Will lay sprawled out on the couch. His eyes were on the TV.

  “Where’s Nicole?” Josh asked, sitting down.

  “She left. Said she had to go ge
t some things.” Will held the remote out in front of him and surfed through the channels. Not once did he look at Josh.

  “Oh, okay.”

  “Look, Josh, I don’t know what Nicole told you, but know this: I am getting my threesome. While I wanted it to be with Nicole and another chick, tonight you are that chick and I’m going to treat you as such. Understand?”

  “I do.”

  “So don’t complain when my dick is in your mouth or in your ass.” He had seen this side of Will before. He would get like this when work really stressed him, or when too much time had passed since he last had sex with Nicole.

  Josh said nothing as he got up and returned to his bedroom. He opened his closet and stared at the red dress. Minutes passed by until he finally removed it from the hanger and stepped into it.

  The material was light and delicate. Soft and stretchy, it left nothing to the imagination. After zipping up the back, Josh had to pull the hem of the dress down to cover the tops of his stockings. He looked at his reflection in the mirror and frowned when he saw his absent cleavage.

  He turned and looked at his body from several different angles until he heard the door to the apartment open and close and Nicole’s cheery voice. She was excited about something, and whatever it was, it brightened Will’s mood.

  Josh turned toward his door, his eyes spotting the unopened brown box on his desk. They lingered there, refusing to budge. The dildo was supposed to be part of a trial run to see if he would actually enjoy anal.

  But now there was no time for a preliminary. Josh was running the race for real.

  He heard a light tap on his door. “Josh? You okay?”

  It was Nicole. She had changed out of her warm winter clothes into something more alluring—something that created a different kind of heat, as evidenced by the clacks of her heels.

  “Josh?” Nicole’s voice was quiet and apprehensive. The knob turned slowly and she poked her head in. He said nothing as he looked away from the door. “Jo—Holy crap!”

  She flung the door open and stood in the frame, eyes alight and hands covering her agape mouth. Nicole was beyond excited. Josh could feel the weight of her gaze and he faced her, only to avert his eyes moments later.