Lipstick & Miniskirts

by John Dylena

  David sat quietly in the passenger seat as Sara drove home. In his head, he was going over what had transpired earlier at the mall.

  Something that bothered him greatly.

  He’d looked over at Sara and smiled warmly. She was a beautiful woman with long red hair, flawless skin, a great body, and a killer intellect to boot. He’d thought he had won the lottery when she’d agreed to go out with him, and again later when she’d become his girlfriend.

  But the problem wasn’t that he was still attracted to her. It was the men they saw while at the mall.

  Guys with chiseled jaws and ripped, muscular bodies; men with thick, bushy beards, clean-shaven faces, or even that rough stubble that’ll give you goosebumps when you rub your hand on his cheek.

  More than once, David had caught a guy checking him out, looking up and down his body with keen interest and flashing him a smile that made him weak in the knees and his panties wet. Too often, he caught himself staring at the images of the models advertising underwear or suits. He bit his lip as he imagined what having sex with another man was like; when his pussy would be filled with a real, pulsating cock and not an inorganic toy.

  But even though he was constantly fighting those newfound lusts in his mind, every time he’d set his eyes on Sara, they would disappear, and all he would be able to think about was her naked body and they way her fingers made him squeal with girlish delight.

  He wondered if this was how every woman felt, or if he was a victim of a curse that turned him into a horny slut with an insatiable thirst for sex and pleasure, no matter the gender of his lover.

  This question remained with him as he stepped through the doors of the bar with Sara. Would he walk away in her arms, or in the arms of a man he would meet here tonight? Tomorrow morning, would he wake up still attracted to Sara, or would he find himself no longer interested in women, only men?

  Or perhaps this was all a bad dream, and he would wake up tomorrow back in his male body with Sara beside him.

  But none of that mattered now. What mattered was that he was walking in between the tables and chairs in a short, gray dress and matching pumps. In his hand was his purse, filled with everything a girl needed, according to Sara. His long brown hair was styled in a loose up-do and his nails were painted and manicured. David was never a fan of the smell of nail polish, and sitting in the salon watching the women work on his fingers and toes while another cut and styled his hair had been an overwhelming experience.

  Sara had done his makeup. She’d chosen a dark red hue for his lips and a soft, earthy-brown for his eye shadow. Chandelier earrings hung from his lobes—whatever magical force transformed his body also pierced his ears for him. In appearance, he was ready for a night on the town, but he wasn’t sure if he was mentally ready for one.

  David was a lightweight even when he had a male body, and unlike Sara, who could drink men under the table, he was still a lightweight. It was something he discovered only after he found himself chatting with a man named Richard.

  Richard had blond hair and steel-blue eyes that were open and welcoming. Sara brought him and a friend of his back to the table when she left to get another round for the two of them.

  David looked over at her when Richard turned his head away to cough. Sara was happily chatting away with the other guy. He had no idea what she had planned when she brought the two men back, but David’s concerns vanished when he looked back at Richard.

  Richard smirked, then broke into a grin as he looked away, the flash of his teeth almost blinding David. The way only one of his dimples in his cheeks surfaced from the lopsided angle of his lips gave him chills, and David sunk his teeth into his own lip without thinking about it as their eyes met.

  Those eyes… so deep and fathomless, like an abyss beckoning David with the promise of a warm forever; someplace he could just fall into and never find his way back out of; a place of peace and warmth unlike any he’d ever known.

  David’s heart fluttered in his chest, and he tried to look away from Richard’s stare, only to find himself gazing at his broad, muscular shoulders, instead.

  David wondered without meaning to: what kind of positions could Richard get him into with those strong arms of his?

  “Fiona,” Sara said to him. Then, when he didn’t respond: “Fiona.”

  David blinked as he turned to her. “Yes?”

  “Need to use the bathroom? I have to.”

  It took him a second to register what she meant. “Oh, right. Yes, I do have to go.”

  “Excuse us, gentlemen,” Sara said with a wink.

  “Sure thing, ladies,” Richard replied.

  Sara slid out of her chair with her purse in one hand and other arm wrapped around David’s. He grabbed his purse and followed her to the bathroom.

  Locking the door behind her, Sara turned to David.

  “Falling for Richard, I see,” she giggled.

  David stared back at her, his eyes trying to maintain their focus. “I am not,” he mumbled. “He’s just… pretty.”

  “Look, babe, if you’re not comfortable with this, let me know.”

  He smiled. “Uncomfortable with what?”

  Sara turned away from him and looked at her reflection in the mirror. “I was going to invite them back to our place. I figured it would be fun for you to experience being with another man.”

  “I… I don’t know, Sara,” he said, “I thought we’re boyfriend-girlfriend… err, girlfriend-girlfriend?”

  She took her hands off of the counter and placed them on his shoulders, preventing him from toppling over. “We are, but this is only for one night. I’m not asking you to date him. Just… have sex with him.”

  “But… I love you.”

  “And I love you. If you don’t want to do this, then just tell me and I’ll call it off.”

  “I…” David trailed off as images of Richard naked filled his mind. He imagined himself in the arms of the husky man, his dick filling David’s pussy.

  He shifted, his hands moving to his crotch as if covering an imaginary boner. His already red face turned scarlet as he bit his lip, picturing the man ploughing him on his bed with Sara getting fucked next to him.

  “Fiona?”

  “Okay,” he replied, looking up at her. “But just this one night.”

  “That-a girl,” Sara said with a smile, hugging him tightly against her chest.

  David had barely stepped foot into the entryway of the condo when she turned around, wrapped her arms around Richard, and kissed him. The man was a good foot taller than her, even with the heels he was wearing, and David had to practically jump to get her lips to Richard’s.

  Richard responded by wrapping his arms around David, lifting her off of the ground. Sara and her date came in after them, smirking at David and how eager she was.

  “Fiona, wait until we get to the bedroom!” Sara said, playfully tugging at David’s dress.

  Richard released her and they followed Sara to the bedroom. The two men grinned at each other as Sara and David kissed, removing each other’s dresses as they climbed onto the bed.

  They separated as the two men stripped and joined them. David’s lips sought out Richard’s as he placed himself on top of her, one hand cradling David’s head and the other sliding underneath her bra.

  David squealed as Richard fondled her breast. Richard sat back and watched as David unclipped her bra, tossing it aside and freeing her ample bosom for Richard to enjoy.

  He moved down David’s body, kissing and sucking on her nipples, his hand rubbing the inside of her thighs, inching closer to her anxious cunt.

  David looked away from her lover to Sara, who grinded her hips against her date, her hands moving through her hair as he thrust into her from beneath.

  Her attention shifted from her girlfriend to the man pleasuring her, and David’s eyes went wide when she saw Richard’s rock hard cock appear between her legs.

  She bit her lip as she watched him slide on the rubber. Her pussy hunge
red, longing to be filled.

  “Please, Richard. I want you to fuck me!” she said, rubbing the insides of her thighs.

  “How could I resist an offer like that?” Richard said as he smirked. His devilish grin made David giddy. The bed shook and David looked away once more to Sara.

  She and her date had switched positions, and she now laid on her back next to David. She looked at her as her date fucked her, reached out her hand to rub David’s cheek.

  David stretched her neck and kissed her, pulling away from her strawberry lips to moan as Richard filled her pussy with his throbbing flesh.

  David arched her back as Richard drove into her. Her inner walls gripped Richard’s cock, unwilling to let it go. He pulled out and thrust back in, and David moaned once more.

  She writhed around on the bed, her fingers rubbing her face and hooking to her lips as Richard moved in and out of her, both the pace and force of his movements intensifying until David was lost in a sea of erotic bliss.

  Sara cried out next to her as she orgasmed and her date pulled out of her and looked to David.

  He nodded to Richard, who flipped David onto her belly effortlessly. She looked back at him as she climbed onto his hands and knees, moaning as Richard slapped her ass and gripped her hips.

  David looked away from him to the other man, whose rock hard cock was inches from her face. She closed her eyes and moaned as Sara slid underneath him and rubbed his clit while Richard pounded him.

  Her open mouth was an invitation for the man, and he slid his still-hard dick into David’s mouth. The man’s musky aroma filled her nostrils and her tongue rubbed the underside of his cock as he thrust in and out.

  It felt wonderful being filled at both ends. David had never been a dominant man in bed. The handful of women he had slept with had to make up for his slack, and oftentimes, the adventure ended early before either partner could get their release.

  Now she was on the receiving end, looking up at the man who filled her throat with his thick cock. There was no hesitation, no second thoughts as to why she was wrapping her lips around his throbbing member. All that David could feel was lust—pure, erotic bliss at being fucked.

  The feeling of total submission was liberating. When she was a man, she had refused to accept the fact that she was a bottom—the submissive half of the relationship. She didn’t want to admit that she didn’t have any control in the bedroom.

  But now, all she wanted to do was serve her lover. Fiona was a slave to her lust, her unquenchable libido, and it didn’t bother her in the slightest.

  Oh god, this is so good! Fuck me harder!

  The man in front of her grunted as he gripped David’s head. Seconds later, David felt thick ropes of hot cum shoot out of the man’s dick into her throat, and it was enough to send her over the edge.

  David moaned as she climaxed, coating Richard’s dick with her own juices as Richard pounded harder and harder until he came as well. David swallowed the salty treat as the man pulled out of her mouth and backed away, leaving David licking her lips and exhausted.

  The two men climbed off of the bed and put their clothes back on as Sara crawled over to David. She fell onto her side when she heard the front door close and a warmth spread throughout her body as it changed one final time.

  Sara watched as David’s breasts grew two cup sizes, moaning as her chest filled out to a bouncy set of double-D’s and her dark hair lightened, changing from near-black to platinum blonde. David blinked as she sat up, her eyes turning ocean-blue.

  “I guess I wasn’t done changing,” she said, looking at Sara.

  “David… about the guys…” Sara said, looking away. “I hope I didn’t—”

  Her words were cut off by David as she kissed her.

  “Sara, you are the only one for me. Your cock is the only one I want in me.”

  Sara smiled as she pushed David onto her back. She looked up at Sara submissively and watched as she climbed up off of the bed.

  “Such a slut, Fiona,” she said, walking away and disappearing into her closet. She returned a minute later wearing a different harness with an even bigger dildo than the purple one. “I think you need to get punished.”

  David squealed as she mounted her, filling her sopping wet cunt with her thick dick.

  “I like the new you,” Sara said, rubbing David’s cheek as she thrust into her. “How do you feel, David?”

  “I feel like… Fiona,” she moaned, smiling.

  DOMINATED BY A DEMONESS

  As much as Chris hated it, he couldn’t say no to Amy.

  The blonde-haired, blue-eyed woman stood in the doorway to his apartment, leaning on the door frame as she gripped her substitute purse. She stared at him with half-open eyes and her disinterested sigh reeked of alcohol. Even without the short blue dress and platform pumps that matched her cerulean eyes, Amy was a stunner. Her long hair fell in waves, well maintained and recently styled.

  In the back of his mind, Chris wondered if Amy purposefully said no to the countless suitors at the bar tonight just so she could come back and relieve her sexual frustrations with her neighbor. He hoped it was so, because the alternative would mean that to her, he was nothing more than a sex toy.

  He looked back over his shoulder at his computer and the game that he’d paused to answer the door. It was calling out to him, longing to be played. It had just come out that day to glowing reviews, all of them correct. Chris hadn’t been able to step away from his computer from the moment he’d started playing it, and that was six hours ago.

  It didn’t matter that he didn’t answer her question on whether she could come in. The second he diverted his attention from her, Amy took a step forward, her platform heel clicking on the hardwood floor.

  Chris turned back toward his guest, who pushed him aside as she strolled in like she owned the place.

  “Hey, what are you—?”

  “Oh cram it, nerd,” Amy said, dropping her purse on the accent table by the door. “Got anything to drink in this virgin cave of yours?”

  Chris rubbed his face as he closed and locked the door. “How can it be a virgin cave if the occupant isn’t a virgin?” He rolled his eyes.

  “If it weren’t for me and my generous nature,” Amy began as she busied herself digging through his liquor cabinet. “You’d still be a virgin.”

  “Yes, help yourself,” he said, waving her off. “I bought that just so you could drink it.”

  Chris sat back down in his chair and returned to the game he was playing, trying to ignore the out-of-tune singing coming from his neighbor.

  “Whatcha playing?” she asked him, resting her arms and chin on the back of his chair. “Oh, some stupid R-P-whatever you call ‘em.”

  “It’s called an RPG. It’s short for role-playing… oh, never mind. Like you’d care.”

  “You know what I want?” Amy said, taking a long sip of whiskey. “Your cock.”

  “Damn it, Amy!” Chris shouted as he jumped out of his chair. Amy’s hand fell out of his lap, where a moment ago she’d squeezed his dick through his flannel pants.

  “What’s the matter, Chris? Are you gay now? Is that why you don’t want to have sex with me?” Amy sat in his chair and spread her legs, forcing the hem of her short dress up to her hips.

  Chris opened his mouth to speak, but his gaze fell to the front of Amy’s black G-string.

  “So you are still attracted to women,” she laughed. “Does that make you bisexual?”

  He shook his head, regaining control of his body. “No, I’m not gay or bisexual. I just… don’t like being sexually used by you!”

  He finally said it. Chris exhaled as the weight of his confession was removed from his shoulders.

  For four months, Amy had been coming by his apartment for nothing but sex. The first time happened right after she was dumped by her boyfriend. She’d gone to the local bar, gotten plastered, and returned to her apartment, only to realize that she’d forgotten her purse.

  Chris
had let her into his apartment so she could sleep, but instead, she started kissing him. Being nothing more than a lonely, socially awkward nerd—not to mention a virgin—he hadn’t known what to do.

  Amy had kept kissing him, and Chris had been too sexually frustrated to pass up on the opportunity. That night, he lost his virginity.

  He’d felt terrible for three days following that night, until Amy showed up at his doorstep once more, only this time, she as sober as could be. She told him not to worry about having sex with her, and that she was glad it was only him and not some random stranger. Not only that, but she’d really enjoyed it and wanted to go at it again.

  As time went on, Amy’s polite requests turned into demands. She became more aggressive and dominant during sex. In Chris’ mind, he had become nothing more than a sex toy for Amy to use—a living, breathing dildo. His dreams of asking her out on a date and her becoming his girlfriend faded away.

  But no matter what, he couldn’t say no whenever she showed up, whether she was drunk or stone-cold sober.

  Tonight was going to change everything.

  “Here, hang on a sec. I’ll be right back,” she said, ignoring his comment about being used.

  Chris sighed as he watched her stumble out his door, hoping and praying that she would just go to her apartment, lie down on the couch, and fall asleep. Then he could get back to his game without any further distractions.

  He was wrong.

  Not even five minutes passed before Amy returned. She closed the door behind her and locked it.

  “Did you come back to tell me that you decided against this and instead will be going to bed?”

  “Nope. But I have a proposition for you.”

  “What do you have in mind?” Chris said, rolling his eyes. He kept playing his game, hoping that Amy would just leave him alone. He stopped only when he heard what she had to offer.