Lipstick & Miniskirts

by John Dylena

  But his body wouldn’t let him.

  His bladder screamed at him, and under the very real threat of wetting himself, he reluctantly rolled out of bed and wobbled into the bathroom, his eyes half-open and his mouth agape.

  Just before opening the door, he turned and looked at his gorgeous girlfriend already sprawled out across the space he had vacated. He smiled groggily, recalling the serendipitous events that had brought them together.

  They had met during their senior year of college. Sara was the captain of the girls volleyball team, and David was her tutor. Being a college athlete meant that Sara devoted a lot of her time to the sport and very little to her schoolwork. Many athletes had trouble keeping up in their classes, and so each was assigned a tutor for when they invariably fell behind.

  David didn’t choose Sara, nor did she pick him; they were assigned to each other based on the classes that they took. He wasn’t a nerd, but math came easily to him, so he was more than glad to offer his services to those that had trouble grasping calculus, trigonometry, statistics, or even more basic maths like geometry.

  For Sara, it was calculus that stumped her. She was a business major with dreams of running her own company or becoming the CEO of another. She was charismatic, but firm; a natural leader and decision-maker. Even though she wasn’t the most skilled player on her team, her teammates looked to her for guidance and motivation when things got tough.

  It was her dominant personality that had scared off many a potential boyfriend. She wasn’t demanding or apathetic to their needs—she just liked being the one that held the reins. This didn’t go well for her lovers who wanted to be the ones on top. After several failed relationships with men who inevitably felt too emasculated by her to stay, she began experimenting with a different type of men: the ones who labeled themselves as submissives.

  But even then, the relationships never seemed to work out. Despite the fact that the men were willing to let her set the pace in the bedroom, the sex was disappointingly one-sided; they got what they wanted as she bounced on top of them, and Sara felt like a tool.

  One night after several drinks at a sorority party, Sara found herself in one of the many bedrooms with another girl. She couldn’t remember the name of the girl for the life of her, but no matter how hard she tried, she couldn’t forget the girl’s touch or her strawberry lip gloss; the way she caressed Sara’s breasts or played with her nubby pink nipples.

  The memories flooded back to her when she’d sat next to David during their first tutoring session. As amazing as having sex with another woman was, Sara still found herself primarily attracted to guys. Even on those lonely nights where her only companion was the toy teasing her, she still pictured a man thrusting into her.

  But something was still missing, and Sara continued experimenting, oscillating back and forth between being with a man and having sex with a woman. Neither seemed to fulfill her.

  It was only after a night with a petite blonde that Sara found the happy medium she was searching for.

  That blonde that she’d locked lips with turned out to be a man in drag. She was in his apartment that night, and after the discovery of the cock in his panties, Sara decided to keep going, as perhaps the only thing she hadn’t tried was being with a man dressed as a woman. She was so hell-bent on finding that missing piece in her sexual puzzle that it didn’t matter who it was that she slept with, as long as her lover showed her something new.

  She found the missing piece in the form of a strap-on dildo.

  After eating her out, the man asked if she would fuck him with it, and Sara obliged him. Nothing satisfied her so much as pegging, but unfortunately, after the night of her sexual epiphany was over, no one else would give her the opportunity.

  That was, until she met David.

  He was a thin man with an average build, and shorter than she was. Every man that she had been with, except for the transvestite, had been taller than her with firm, toned bodies. They were all athletes like she was, too.

  But David was no athlete. He was just an average guy with an above-average intellect. He was also shy and introverted, traits that Sara quickly noticed when they’d first met in one of the many study rooms in the school’s library.

  She was late to their session. Practice had run longer than planned, and she’d had no time to change. The look on David’s face when she’d opened the door to the study room wearing a t-shirt and gym shorts was one that she’d never forget.

  Even with his kind and tolerant approach to tutoring, Sara was difficult to work with. When she couldn’t grasp a concept as easily as she’d have liked, it angered her.

  It was his hair that brought the memories of Sara’s first night with a woman back to her. The woman that had launched Sara’s journey toward bisexuality had hair just like his: light brown and thick, with a little curl to it. David’s eyes were brown as well, and they had a hard time staying on her face, especially with the tight shirt she was wearing.

  As the semester went on, they began chatting more and more outside of their study sessions, and Sara wondered why David never asked her out. She just figured it was his shyness, and she decided to wait and see if he would overcome it. She continued her sexual journey without him, using it to release her pent-up stress from both her academic and athletic challenges.

  It wasn’t until three months after school had ended that David contacted her again. Sara had landed a corporate job and was already on track for a promotion when she got his text message. She was still single, and since she was no longer surrounded by men and women her age on the small campus she’d graduated from, her sex life had come to a screeching halt.

  She was more than happy to take David up on his offer to buy her a drink and catch up. Later, at that bar, she finally learned why he’d never asked her out: he wasn’t allowed to. If he had, he not only would have lost his job as a tutor, but he would’ve lost his scholarship, as well.

  “That doesn’t matter anymore,” she’d said, leaning toward him. “What matters is that I have an itch that’s been waiting a long time to get scratched.”

  One drunken night of passionate sex, several dates, and a year later, David moved into Sara’s condo. They had only been living together for two months, but things between them were wonderful.

  Until the incident.

  Turning away from Sara, David shuffled into the bathroom, blearily flicking on the light switch. He immediately regretted it; the bright white lights blinded him, searing his corneas with their potent light. When his vision returned, he pulled down his pants and lifted up the toilet seat.

  He reached for his dick, but there was nothing to hold onto.

  “Holy shit!” David screamed, bending over and looking closely at his groin. His outburst roused Sara from her sleep, and she sprinted into the bathroom.

  “What? What’s the matter babe?” she asked, rubbing her eyes.

  “Look! My dick is gone!”

  He pulled at his hair, utterly confused. His heart raced in his chest as he stared down at his groin. He didn’t know what to do, how this had happened, or what it meant. Sure, people often joked that he was the woman in the relationship, but now he was literally the woman.

  His entire life flashed before his eyes. What were his friends going to think? The people he worked with? His eyes darted about as panic started to set in.

  He was on the verge of passing out when Sara’s touch brought him back down to earth.

  “Wha—oh my,” she replied squatting. “Yup, that’s a vagina.”

  She reached out and touched the flesh between his legs, her fingers delicately circling the pink folds.

  “Ohhh,” David moaned. His knees buckled as his girlfriend examined the cleft. She couldn’t help but smile when she heard him moan from her touch.

  “That’s real, all right,” she said, standing up. “I don’t know what else to tell you.” She looked down to see his legs shaking.

  “David, why don’t you relieve yourself? Then we can d
iscuss this further.”

  “But—”

  “Just sit down and let it flow.” She took her hands off of his shoulders and walked out of the bathroom, closing the door behind her.

  Sara put her back to the door and rubbed her face with her hands. This is going to be a problem. But it’s not necessarily a bad thing.

  Every now and then since they’d started dating, Sara had longed for the touch of a woman. He was fine letting her take the lead in bed, and he did what he could to ensure she was satisfied, but David was no woman. As attentive as he was in bed, he lacked the delicate touch of a more feminine partner, not to mention the body of one. Sara craved the smell of a wet pussy and the skilled tongue of a woman who knew what buttons to push to make their partner melt.

  Maybe this is a blessing in disguise.

  She backed away from the door and sat on the edge of the bed to wait for the return of her boyfriend.

  David opened the bathroom door slowly. His head hung low and his shoulders slumped. He looked utterly depressed, as if everything he had ever loved just vanished or died.

  “I… I don’t know what to do,” he said numbly. “I just feel so… empty.”

  Sara patted a spot the bed next to her. He lifted his eyes to her face and couldn’t help but smile. Her red hair was loose and fell past her shoulders in an odd mix of curls and waves, and her green eyes sparkled in the morning light.

  She smiled at him. It was a warm, comforting smile that made the darkness in his mind dissipate. Sara had always been there for him when times were tough. Despite her dominant personality, she had a sensitive side—one that she never showed to anyone but him.

  He sat down on the bed next to her and looked down into his lap.

  “I don’t know how it is you woke up this morning with lady parts,” Sara said, wrapping her arm around him. “But we’re going to work though this together.”

  “But—”

  “Shhh, David,” she said, putting a finger on his lips. “Being a lady isn’t all that bad. You know I am bisexual, right?”

  “Yes, you’ve told me that, but what does it—”

  Sara grinned wickedly. “It means that I know how to pleasure a lady.”

  She turned toward him, her right hand slowly creeping up his thigh as she stared deeply into his eyes. She leaned forward as her fingers slid underneath the elastic band of his flannel pajama pants.

  “Sara,” he began. “I don’t think this is a good ide—Ooooohhhh!”

  David threw his head back and moaned loudly as her fingers rubbed the delicate flesh between his legs.

  “Oh, babe, you’re soaking wet down here,” she said, gently teasing the silky pink folds. David fell onto his back and writhed under the expert touch of his girlfriend. Sara kept her eyes on him, watching him squirm and moan. “See? It’s not so bad being a woman, is it?”

  She pulled her hand out of his pants and stood up from the bed, stopping when she heard him whimper.

  “Please… don’t stop,” he whispered. Then he looked away from her, his face bright red.

  “As you wish,” she replied.

  Sara stood in front of him and grabbed the waistband of his pants, pulling them slowly off of his legs. She grinned when she saw the tender flesh and the tiny beads of his juices darkening the sheets. She tossed his pajamas aside and climbed up onto the bed next to him.

  He looked up at her fearfully, and she smirked in response.

  I’m going to rock your world, David.

  She bent down and placed her lips onto his, kissing him passionately as her hand caressed his inner thigh. Her fingers circled the delicate cleft as her tongue explored the depths of his mouth, her left hand sliding up underneath his shirt.

  David moaned as she rubbed his outer lips with her index and middle finger, moving slowly up and down while her thumb traced the crown of his womanhood. She pulled away from his mouth and looked down at him as her thumb made tiny circles.

  He was powerless. She had him completely under her control, and she loved it. The way he bit his lip as he squirmed from her touch made her push on. She wanted to hear him cry out when he reached that peak; to watch his body flail as overwhelming pleasure coursed through his veins and flooded his brain. She wanted to see him lose himself in pure, carnal bliss.

  Sara’s thumb rubbed his hard nipple while her right hand continued to play with his sopping wet cunt. He was almost ready.

  Picking up the pace, she stroked his clit through the hood as her fingers moved inward, gently stretching apart his inner folds, exposing the hot pink flesh of his pussy. Memories flooded back to her of when she was in his position, particularly of that drunken night at the sorority house when she was the one squirming and moaning.

  She felt David’s nipple harden even more as she squeezed it and pinched it slightly, and his body convulsed beneath her ministrations. His eyes opened, and his cry of ecstasy bounced off of the walls of the bedroom. He arched his back as Sara slid her two fingers into his vagina and rubbed the velvety lining of his hot, wet sheath.

  “Oh, god!” he yelped.

  Sara moved her fingers faster, grinning as she rubbed the little bulb swelling inside of his pussy. So close, David. You’re almost there.

  She pinched his nipple once more and his legs thrashed spasmodically on the bed. His eyes rolled back into his head as he climaxed, coating Sara’s hands with his sweet release as unfathomable rapture pulsated throughout his body.

  Sara removed her hand from his quivering cunt and admired her handiwork, but her smug grin disappeared as David’s body began to change.

  He laid on the bed, his chest rising and falling rapidly as his heart raced. His eyes stared blankly ahead, so physically drained that he failed to notice the transformation running rampant through his form.

  Sara covered her hand with her mouth as she watched. The little body hair he had receded back into his skin, his waist narrowed, and his hips widened slightly, turning his already thin build androgynous.

  David’s chest swelled until tiny A-cup breasts poked through his shirt. His short hair grew until it passed his ears and his facial features softened, giving him a more feminine appearance.

  “Oh my god,” she breathed. “David… Your body…”

  He sat up on the bed, rubbing his face. “What?” He coughed; his voice had become lighter and more delicate. “What the fuck?!”

  David lifted his shirt up and examined his body. His hands traced his curves and cupped his flat breasts.

  “I have breasts!”

  “I wouldn’t call those breasts,” Sara laughed.

  “Sara! This isn’t funny.” David crossed his arms and pouted. “I’m turning into a chick.”

  She continued laughing. “I think you became a chick when you woke up this morning with a pussy. You’re just become more feminine. Although, with the right outfit and makeup, you could look incredibly sexy...”

  “No, I’m not wearing any of your clothes.”

  Sara’s face lit up. “I wasn’t even suggesting that, but now…”

  She grabbed his wrist and pulled him up off of the bed. Even when he’d still had the body of a male, Sara had always been stronger than him. She’d kept working out even after finishing college and hanging up her volleyball career, whereas he’d never really had an interest in hitting the gym.

  Sara easily pulled him off of the bed and onto his feet. Seeing him standing in front of her with tits and a pussy brought on another bout of laughter from the fiery red-head. It didn’t help that David had shrunk down to where his eye-level was just above her breasts.

  “David, babe, you know I was the only girl in my family, not to mention the youngest. Growing up, I always wanted a little sister to play dress-up with. But this is even better!”

  “Do I have to?” he whined. He looked away from her. “I mean, it’s bad enough that I’m no longer a man.”

  Sara put her hands on his shoulders. “David, answer me this: did you honestly believe you were the m
an in this relationship? Besides, even though you’re now a chick, I still love you.”

  He opened his mouth to speak, but closed it when he realized that she was right. Looking back on the time they had spent together, Sara had always been the dominant one, although he was no pushover himself. Even so, it never bothered him that she was the one who so often took charge. He never liked being a decision-maker, and Sara was more than happy to make them in his stead, though she never did so without his input.

  “I guess you’re right,” he sighed. “And if this is permanent, I might as well get used to wearing women’s clothes.”

  Sara beamed. “That’s the spirit! Don’t worry, David. This will be a lot of fun. You know I have plenty of sexy outfits, and I’m sure they’ll look great on you. Go ahead and take off your clothes and wait for me to find something for you.”

  David frowned. “Okay. Just… don’t get me something that’s overly sexy.”

  “You’ll wear what I give you to wear,” she said, disappearing into her walk-in closet.

  He slowly peeled off his shirt, twitching when the fabric of his top rubbed against his sensitive nipples. He brought his knees up to his chest and curled up into a ball while he waited for Sara.

  She returned carrying a pair of red satin panties and a matching bra. “This bra is the smallest one I could find.”

  David took the panties from her as he stood up. He held the garment in his hand, his thumb rubbing the soft, thin fabric. He’d handled her panties many times during their relationship, but in nearly all of those cases, it was when he was taking them off of her.

  Now he was putting them on himself.

  Sighing, he stepped into the leg holes one at a time and pulled the panties up to his waist. He squirmed. The delicate fabric tickled his hairless legs and gently rubbed his virgin cunt.

  “These are actually pretty comfortable,” he said, looking back as his ass over his shoulder.

  “I was going to have you wear a thong, but those can come later,” she said with a smile.

  Next, Sara handed him the bra. He slid his arms through the straps and she stepped behind him and clasped the back.