Lipstick & Miniskirts

by John Dylena

  “How’s it feel?”

  “Not too tight,” he replied, testing out the lingerie.

  “Shame you’re so flat-chested,” Sara said, peeking into the cups of the bra. “We could always get you implants.” He grimaced, and she laughed. “Hang on while I get the rest.”

  She returned to the closet and David walked over to the mirror in the corner of the room. He stood in front of it and inspected his body. The longer he looked at it, the more he realized that he had the body of a girl just starting puberty.

  His curves were lacking and his breasts were just barely noticeable. His hair was longer, but it was still short and his voice reminded him of his own before he went through that developmental phase. God, I hope I’m not regressing.

  David’s attention shifted to Sara as she exited the closet.

  “Oh, you’ve got to be kidding me,” he muttered.

  Sara held in her hands a plaid miniskirt and white button-down blouse. “What?” she giggled. “I thought you liked slutty schoolgirls.” When he didn’t share in her laughter, she sighed and rolled her eyes. “All right. I’ll find something else.”

  She returned to the closet and put the clothes back where she’d found them. Digging through her dresser, she moved a pile of her panties out of the way and froze, her eyes glued on the long-forgotten toy lying beneath them. Sara smiled as she took the harness and purple silicone dildo out of the drawer and set them on top of the dresser.

  She stripped out of her pajamas and quickly put together an outfit. She wore a black lace bra and panties, dark stockings with lace garters, and matching black thigh-high boots. Zipping up the backs, she beamed, anxious to surprise David.

  With her eyes darting back to the toy, she grabbed a pair of white stockings, red platform heels, and to top it all off, a long-sleeved, white fishnet dress. He’ll look so sexy in this, she thought.

  Items in hand, Sara stepped out of the closet back into the bedroom, where she found David sitting on the bed, playing with his new bra.

  “Here you go, David,” she said. “Put these on.”

  “Okay, sure—whoa!” He sat up. His eyes nearly bugged out of his head. “Damn, Sara. You look sexy!”

  She winked as she tossed him the stockings and set the shoes and dress on the bed next to him. He stared at the shoes, and wondering how in the hell he was going to be able to walk in those.

  “David, eyes on me,” she said, grabbing one leg of the stockings. “I’m going to show you how to put these on.”

  Holding one of the white stockings in his hand, he followed her instructions and rolled it up in to a donut. Then he lifted his right leg and watched her slide it up.

  David bit his lip. The thin, clingy fabric of the stocking sent waves of pleasure throughout his body. He always loved it when Sara wore stockings. She had such great legs for them.

  He eyed his own leg, reveling in how feminine it looked with the snow-white thigh-high on it, and mimicking her movements, he pulled the other stocking up his leg.

  “You have amazing legs, babe,” Sara said, appreciatively stroking his calves and thighs. “Allow me.”

  She grabbed one of the high heels and slid it on him, giggling as his shapely foot disappeared into it. “My own Cinderella,” she purred. “Ooh, maybe I should have you wear a prom dress. I could dress you up like a princess!”

  “I’ll have to pass on that one,” David said, watching her fit the other pump onto his left foot. “It was hard enough convincing myself to put on the lingerie.”

  “Oh, I think in no time, you’ll be begging to wear the dress.” She helped him onto his feet and held onto his hands as he tried to balance in the six-inch heels. “Don’t worry. You won’t be in these for long,” she said, pulling the fishnet dress over his head.

  “What does that mean?” he asked, pulling the hem of it down to his thighs. “This doesn’t cover much, does it?”

  “Not really,” she said, walking away.

  “Then why give it to me?”

  “Because,” she answered, poking her head out of the walk-in closet, “it makes you look incredibly sexy.”

  David leaned back, trying to look inside the closet. “Sara?”

  He received no reply.

  Shrugging, he took a couple of steps forward. He was so busy trying to master the art of walking in heels that he never heard her exit the closet.

  “Hey, Sara,” he said, looking up. “I think I got it…”

  He trailed off when he spotted her leaning on the closet door.

  “Holy shit.”

  She turned, putting her back against the door as she swiveled her hips outward. David watched her hands move down her belly to her hips, where they gripped the base of the lavender cock jutting out from between them.

  It had been months since she’d worn that harness. The last time he saw it, she’d plunged it into his ass minutes later. As much pleasure as it brought her, it did little for him. He’d felt bad when he’d told her that he hadn’t enjoyed it. After that night, he’d never seen the toy again.

  Until now.

  Sara moaned quietly as she stroked the shaft of the dildo with both her hands. It was anatomically correct, with a bulbous head and spider web patterns of bulging veins. David swallowed as he watched her play with it, remembering that it was double-ended.

  “Seeing you dressed in that sexy lingerie got me hard,” she said, pushing herself off of the wall.

  She kept her eyes on him as she sashayed across the bedroom. She sat down on the edge of the bed and spread her legs apart, her hands rubbing the insides of her thighs.

  “I’d love to see those pouty lips of yours wrapped around my cock,” Sara said, licking her lips. “How about it, babe? Would you like to give me a blowjob? If you’re a good girl, I just might pop that cherry of yours.”

  David’s heart pounded so hard in his chest that he could hear it. His mouth went dry as his eyes remained glued to her violet dick.

  He took a step forward, feeling himself pulled toward it. He was caught in her tractor beam, and what frightened him the most was that he didn’t even try to fight it. He allowed his feet to move closer, the clicks of his heels echoing through the bedroom.

  David’s mouth hung open, his lips squeezing together to form a fleshy “O.”

  “That’s my girl,” Sara said, watching him kneel down in front of her.

  He looked up at her from in between her legs, his hands nervously gripping her strong thighs. She leaned forward and rubbed his cheek with her thumb, smiling warmly.

  “Don’t be afraid, David,” she said softly. “Just go slow.”

  He took his eyes off of hers and focused on the purple toy inches from his face. Never before had he ever considered sucking a cock, even if it was just a fake one worn by a woman. David never found men attractive at all, yet here he was now, staring down the shaft that he was about to wrap his lips around.

  Even if I do continue to change, I don’t want to lose her. I want to be able to still love her, even if I start to develop an attraction for men. Whatever is happening to me, it’s changing more than just my body.

  David leaned forward and slid his lips over the head of the toy, looking up at his girlfriend for approval. She cooed, placing her hands on the back of his head and urging him further.

  He dropped further down the shaft, reaching the halfway point before retreating and removing the cock from his mouth. David stared at it, the top half glistening with a coat of his saliva.

  “Lick it and give it little kisses. Remember what I did back when you had a cock?”

  “I do,” he said, his gaze darting between her prick and her eyes. Then he took a deep breath and plunged right back in.

  He squeezed her muscular thighs as he licked the underside of her shaft, his tongue tracing the head. He planted his lips on her crown, gently kissing and sucking on the glans before inserting the shaft back into his eager mouth.

  Bobbing up and down, David took more and more into his mouth w
ith each pass until he felt the head on the back of his throat. I guess this body doesn’t have a gag reflex, he thought as he slid all the way down to the base, kissing the harness that Sara wore.

  “Damn, babe. You’re an eager slut, aren’t you?” Sara said, her fingers gliding through his hair. “I think you’ve earned a reward.”

  He slid back off of her cock, the glans coming out of his mouth with a pop. The entire shaft was coated with his juices and his eyes widened when he realized what he had just done. The toy was now primed and ready for penetration.

  “Up on your feet,” she commanded.

  David climbed into his feet and stood before her. Before he could say anything, she wrapped her arms around him and kissed him, her tongue snaking into his mouth and exploring its depths.

  He melted in her strong arms. Sara was always a great kisser, and as he tasted her lips, a warmth spread throughout his body. He moaned as her hands moved down his lower back and squeezed his feminine ass.

  In one swift movement, she lifted him off of the ground and dropped him onto the bed like a groom bringing his bride into the honeymoon suite.

  He giggled as she climbed on top of him, her strawberry hair cascading over him like the canopy of a willow tree.

  David looked up at her and smiled. I’ve never seen her so happy. Maybe this isn’t so bad, after all.

  She lowered herself onto him and kissed him passionately, her lips moving down his neck and to his chest. She continued down his body, kissing his stomach and pelvic mound. He squirmed anxiously as he watched her lift the hem of his dress up to his waist and hook her fingers into the waistband of his panties.

  Sara said nothing as she slowly pulled them off of his groin and legs, lifting them into the air in the process and resting them on her shoulders.

  “Oooh!” he screamed as she buried her head in between his legs, wrapping her arm around his left leg and covering his tender flesh in countless kisses.

  David gripped the sheets as he felt his body catch on fire, ignited by Sara’s lustful touch. She had the opportunity to not only satisfy her lesbian cravings, but to do so without breaking the monogamous bond that she shared with David.

  Sara parted his outer lips and lifted up his tiny clit hood with her fingers, giving her tongue access to the sensitive pearl beneath it. He replied to her exploration with a drawn out moan as he gripped the sheets so hard his knuckles turned white.

  She smiled from in between his legs, her tongue flicking back and forth. Her fingers moved to his inner lips, tenderly pulling them apart and fully exposing David’s pussy.

  “Oh… Oooooh!” he wailed as she serviced him. He arched his back as two of her fingers slid into his cunt and rubbed the lining of his sheath.

  That’s right, David. Get nice and wet for me. She grinned as she felt his insides moisten.

  “No, don’t stop,” he said, lifting his head off of the bed as she slid her fingers out.

  “I won’t,” she replied, sliding out from under his legs.

  Sara spread his legs as she scooted closer to him, lined up the head of her silicone cock with his dripping hole, and buried herself inside of him. She thrust her cock all the way in to the base and pulled back slowly.

  “Oh god, yes!” he moaned, reveling in the hypnotic pleasure of being filled.

  She grinned as she pushed her hips forward again and again until she was pounding him rhythmically. Her hips rolled back and forth in a wavelike motion as he writhed underneath her.

  His honey-sweet cries were the fuel to her engine, and with each luscious outcry, she increased the force behind her thrusts until the bed was rocking and the other end of the dildo buried itself deep within her.

  Sara’s hands slid up his body underneath his bra where they squeezed his petite breasts, her thumbs flicking at his rock hard nipples.

  “I… I’m going to cum!” he warned her, panting like a rabid dog.

  “Moan for me, David!” Sara replied, tapping into the last reserves of her energy to push them both over the edge.

  “Ohhhhhhh!” David moaned as his body convulsed and waves of pure carnal bliss flooded his body and mind. His legs shook as his juices flooded out of his stuffed pussy, coating Sara’s cock with his sweet release and darkening the sheets below them. She pulled out of him and fell back onto her ass, watching in awe as his body changed once more.

  David’s brown hair grew until it pooled beside his head, darkening from a light brown to a shade just shy of jet black. His waist narrowed and his hips widened, giving him a much more defined set of curves. Bolts of energy shot though his body as the skin around his chest tingled.

  He lifted his head up off of the bed and watched as the cups of his bra were filled by the breasts that swelled up from his chest. The transformation was pleasurable, and he squirmed as a heat filled his body, clouding his mind and making him giggle mindlessly.

  His features softened once more as his ass expanded, lifting his curvy hips off of the bed.

  In less than a minute, David’s body now matched what he had in between his legs. He was no longer androgynous; instead, he had developed into a full-fledged woman, shedding what little masculinity his body had held onto.

  Sara sat up on the bed. “Oh my god, David. You’re… You’re… hot!”

  “What?!” he shrieked, opening his eyes. He shot up at the sound of his female voice, only to be thrown off by the added weight on his chest. He looked down and squeezed his breasts. “I take it I’m a woman now?”

  “An incredibly sexy one at that,” she said, sitting down next to him. “I mean, look at that body—and those curves! They’re more than enough to make a man melt.”

  “Gross! I’m not gay, Sara,” David said, turning away from her.

  “It’s not gay if you’re a chick, which you definitely are. Now you’d only be gay if you were attracted to me.”

  “I… I’m not into men, okay?!” He jumped up off of the bed and turned toward her. “I still love you, even though now I have a woman’s body—which I still don’t even have an answer for. Do you remember what happened last night?”

  Sara squinted, trying to navigate through the thick brume clouding her mind.

  “No, I don’t. I remember showing up at the bar with you and drinking. Then nothing. Between waking up this morning and arriving at the bar, everything is foggy.”

  “Why is this happening to me?!” David cried. He covered his face with his hands and fell onto the bed.

  “Until we figure this out, why don’t we make the best of this situation?” Sara suggested. “I mean, look at it as a chance to start over, or to experience something new.” She bit her lip. “But I can’t go calling you David anymore.”

  He looked up at her from behind his hands. “But my name is all I have left of the man I once was. You can’t take that from me.”

  Sara wrapped her arms around him. “We still have our memories and photographs. Oh, I’ve got it.”

  “What?”

  “Fiona. I think that should be your new name.”

  “Fiona?” David sniffed. “I… I don’t know.”

  “I like it. And it’s sexy. It rolls nicely off the tongue. Fiona.” Sara stood up and held out her hand. “Come on, Fiona. Let’s go to the mall and get you some new clothes. Then tonight, we can go out to the bar, have a few drinks, and enjoy this very unique opportunity. What do you say?”

  “I guess you’re right,” he replied, wiping away the last remnants of his tears. “This could be fun. I was a plain and boring-looking man. Now I’m a sexy woman.”

  “That’s the spirit, Fiona!” Sara said, jumping up excitedly. “Let’s go shopping!”

  “When you said let’s go to the bar, I thought you meant a casual night out, not that we’d go looking to get laid,” David said, holding up his new dress.

  “I want you to look sexy. I want everyone to be jealous that this hot piece of ass is mine,” Sara said, squeezing David’s plump ass. She leaned over and whispered into his ear. �
��I say we go into the changing rooms and I help you strip. What do you say?”

  “How about we wait until we get home?” he whispered back. “Then I can give you a more private dance.”

  Several hours later, David and Sara emerged from the mall, their legs sore and their hands full of shopping bags. As they’d navigated the labyrinth of shoes, dresses, lingerie, tops, and bottoms, David had eventually relaxed, and he found himself enjoying the outing with his girlfriend.

  It was exactly what their relationship needed. The couple had fallen into a humdrum routine that planted the seeds of doubt in Sara’s mind. David was a wonderful man, but at home, and especially in bed, he was lackluster and apathetic.

  He didn’t share the same drive and ambition that she had. He was a very mellow individual who was content with his life remaining exactly the way it was. She worked hard every day at her job, and when she would come home, she wanted someone to be there for her; to help her wind down and “relieve some stress,” as she often put it.

  David worked from home, and even then, he worked very little. She would come home to him playing a video game or watching TV, and he would rarely ask her about her day or notice that she got a new haircut.

  The more she thought about how they were moving apart, the more often her brain would remind her of the skillful touch of the sorority girl, or the power she felt when she fucked the crossdresser.

  She loved David, and the last thing she wanted to do was cheat on him. He was a nice guy who didn’t deserve that, but relationships are two-way streets, and if he wouldn’t give her the love and attention she needed, then she would eventually have to find it somewhere else.

  On several occasions, she had tried to bring it up, but he would change the subject. Sara didn’t know if he was oblivious to her needs, or if he just chose to ignore them.

  Last night was the night. She was going to break up with him and end it all. It had been too long since they’d last had sex, and Sara had so much sexual frustration locked up inside of her she was about ready to burst.

  Except, the morning after, she’d woken up back in her bed with David screaming about his dick disappearing. When she’d laid in bed next to him after fingering him to his very first female orgasm, she’d smiled as she forgot about all the troubles they’d been having. This was the change she’d been looking for in him. It was a chance for them to rekindle their relationship, and she wasn’t going to let that chance slip away.