Lipstick & Miniskirts

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Lipstick & Miniskirts Page 3

by John Dylena


  Jacqueline laughed. Now that was the Melissa that she—well, Jacob—knew.

  “It’s okay,” she said. “I… don’t mind it at all.”

  The smile returned to Melissa’s face, and she slid closer to Jacqueline. “Oh? Is that so? Well, tell me, Jacqueline, what would you like to do next? We can keep chatting if you’d like. Still several hours left to go in the party.”

  I’m not sure how many hours I have left in this body, though.

  “Well, Melissa, what would you like to do?” Without thinking her hand settled on top of Melissa’s as she spoke. It wasn’t until she became the recipient of a raised eyebrow and pointed glance down that she realized what she had instinctively done, and Jacqueline yanked her hand away in embarrassment. “Oh, I’m sorry!”

  “Don’t be,” Melissa said, gently taking Jacqueline’s hand back. She smiled and lifted her other hand toward Jacqueline’s face. “May I?”

  Jacqueline nodded. Melissa brushed her hand across Jacqueline’s cheek and combed her fingers through her hair, gently twining the soft strands around them before moving on. She could feel the heat on her cheeks as Melissa’s hand cupped her jawline and a thumb brushed across trembling lips.

  “You’re a very beautiful woman,” Melissa purred. “I could get lost in those eyes.”

  She dropped her hand back into her lap alongside of the other, clasping Jacqueline’s between them both.

  “In those stories you’ve read, was there anything that really made you squirm in your chair when you read them?”

  There was plenty that Jacqueline could suggest. She had read countless short stories of the dirtiest lesbian BDSM smut you could find online, webcomics and the longer romance stuff, too. When she was a guy he masturbated to countless porn videos and even commissioned a handful of artists to draw some sexy pictures for him. She was well aware of many different kinks and fetishes. In her brief walkthrough of the dungeon while Melissa led her to this quiet corner, she saw a handful of things she would like to try out.

  “I’d like…” she said, her voice trembling a little, though if it was from nervousness or anticipation—or maybe even both—she wasn’t quite sure. “I’d like to try… orgasm denial bondage.”

  “Very well,” Melissa grinned, lazily stroking Jacqueline’s fingers as they talked. “Before we play, we must negotiate. Do you have any injuries or areas I should avoid?”

  Jacqueline shook her head no.

  “Any traumatic history that I could accidently trigger?”

  She shook her head again.

  “Do you have a chosen safeword?”

  She shook her head a third time.

  “I have my own personal safeword, but I save that for special partners. The go-to safewords are “yellow” and “red”. Yellow means I’ll slow down, red means I’ll end the scene immediately. Since this is our first time together, and your first time ever, we’ll go slow and I’ll check in on you often, okay?”

  Jacqueline nodded her head.

  “Good. For the rest of the scene you must call me Miss, understand?”

  “Yes, Miss.” Jacqueline responded.

  “Good girl.”

  The simple words sent a rush through her body. She almost shivered from the joy and anticipation. Melissa smiled and stood, Jacqueline’s hands still clasped between her own as she guided her to her feet.

  “Let’s see if we can find an open station to use. Do you have any of your own gear?”

  “No, Miss.”

  “That’s fine. I figured as much. I have my own stuff, so no worries.”

  Melissa led her out of the quiet corner and back into the dungeon. She wove through the building, in and out of rooms until they found a suitable piece of vacant furniture. It was a St. Andrew’s Cross, tall and X-shaped, with black leather padding and a D-clip at the top of each arm. Melissa let go of Jacqueline’s arm, and even though she only wandered a few feet away, Jacqueline suddenly felt incredibly alone without her touch. She returned with a spray bottle filled with a clear liquid and several paper towels.

  “Go ahead and wipe down the equipment to make sure it’s clean. You’re supposed to clean it when you’re done, but better safe than sorry. While you’re doing that, I’ll go grab my gear from the bag room. Be right back.”

  Melissa’s hand dragged up Jacqueline’s bare thigh as she walked away. A moment later, she’d disappeared into the crowd. Jacqueline stood frozen like a deer caught in the headlights. All around her the party continued. Several feet away, a man was spanking another with a wooden paddle. In one corner, a woman straddled the lap of a man as she put lipstick on him. Everyone existed in their own little bubble, unaware of what was going on around them or of the woman who’d been a man just a couple of hours earlier watching them.

  Jacqueline finally snapped out of the strange trance and remembered her task. She turned around and sprayed down the giant X, meticulously wiping it clean and trying not to get too caught up in the knowledge that she’d soon be stretched across it.

  A man’s voice rose unexpectedly from behind her. “Are you done with this?”

  Jacqueline turned toward him. He was older, probably in his 50’s, his hair mostly gray but his body still in very good shape. He held a leash in his hand. Jacqueline’s eyes followed it back to the completely naked woman standing behind and to the side of him. She seemed to be around the same age as he was, but her eyes were cast down to the floor and her hands lay clasped behind her back.

  “Ma’am?” he repeated.

  Jacqueline opened her mouth to respond, but just then Melissa appeared from behind the man.

  “Sorry, Daniel,” she said. “We’re just about to start using it.”

  “Oh, Mel, I didn’t see you there.” He looked back and forth between Melissa and Jacqueline. Then he smiled amiably and nodded his head. “You two have fun.”

  He turned away and walked off, the woman obediently following behind him.

  “That was Master Daniel,” Melissa said as she set a small gym bag down beside the cross. “The woman is his wife. Lovely couple. She’s very funny. They attend the munch regularly.”

  “Munch?” Jacqueline asked, tossing the used paper towels into a nearby trash can.

  “Causal, vanilla get-together for kink folk. Usually at a restaurant. It’s an opportunity to chat and get to know the local scene better and discuss regular, everyday stuff. You should go to the next one; it’s next Thursday night at the barbeque place a couple blocks down.”

  If only.

  Melissa bent down and dug through her bag until she managed to produce four cuffs, each made of black leather and trimmed in red fur. She laid them down on the ground in a row and sorted them by size. Then she reached back into the bag, pausing thoughtfully for a moment before lifting out a blindfold and handing it over to Jacqueline as she stood.

  “Up to you if you want to try it.”

  Jacqueline turned it over in her hands and examined it closely. The outside was made of hard black leather, but a layer of black fur on the inside looked as though it would lay comfortably across her eyes. She bit her lip and silently nodded.

  “If you don’t like it, we can take it off.” Melissa gently took it from her and placed it on her head, leaving the blindfold up on her forehead for the moment. Then she bent down and attached the two larger cuffs to Jacqueline’s ankles, her fingers lingering momentarily on the smooth skin of her calves.

  But there was more to be done. “Wrists please,” she said as she straightened.

  Melissa wordlessly wrapped the cuffs around Jacqueline’s wrists and adjusted them. Then she walked her up to the cross and positioned her with her back to the black leather padding, each touch of her hands slow and sensual. Melissa pulled the blindfold down and the last thing Jacqueline saw before the world went black was her happy and eager smile.

  Melissa guided her wrists up to the two D-clips, and after a jangling of metal and two sharp snaps, her wrists were locked in place above her head. Warm hands t
hen slid down the length of latex-clad thighs and coaxed them apart, inch by inch, until finally her ankles found their places and the last of the locks clicked shut. Those same hands found Jacqueline’s hips at the very moment that Melissa’s breath puffed across her ear and raised goosebumps. She trembled, rattling weakly at her restraints.

  “I’m here,” Melissa whispered, her lips close enough to brush Jacqueline’s skin as she spoke. “I won’t leave you. Do not be afraid. What are the safewords?”

  Jacqueline sucked in a deep breath and held it for a moment, trying to steady her breathing. “Yellow and red.”

  “Are the cuffs too tight?”

  “N-No, Miss,” she replied.

  “I like your perfume,” Melissa whispered into the other ear as her hands drifted up her sides, skimming over her body through the fishnet. “It’s so sweet and intoxicating.”

  The world around Jacqueline vanished; the sounds of the party drifted away, becoming muffled and distant in the blackness that surrounded her. The only clear thing was Melissa’s voice. It was finally happening. What Jacob read and fantasized about so many times was finally real.

  Jacqueline shuddered and moaned as Melissa dragged her fingernails along the insides of her thighs, not hard enough to leave marks but more than enough to suck the air from her lungs in a sharp gasp. She lifted the hem of her skirt up to her waist and rubbed her hand down over the front of her panties, briefly cupping her sex before moving on. Jacqueline’s knees buckled as pleasure shot through her. It was beyond anything she had ever felt when she was a man. Her whole body had become incredibly sensitive and every little touch triggered a new jolt of rapture.

  As she squirmed futilely in her bindings, her hardened nipples rubbed and strained against the fabric of her dress. Melissa’s clever fingers explored every inch of her body, from her toes all the way to her scalp. She carefully scraped her nails across the arch of Jacqueline’s breasts, avoiding the sharp nubs that begged for her attention and moving on to her hairline instead, combing her fingers through her hair. Teeth closed gently over the soft flesh of Jacqueline’s earlobe and left her whimpering.

  Jacqueline sensed herself slipping out of the universe. Time held no meaning, and when Melissa finally removed the blindfold, she realized that she had no idea just how much had passed. It took a moment for Jacqueline’s mind to reconnect with her body. She felt weak, panting and sweating. Her legs could barely hold her up. She nearly collapsed when Melissa freed her from the restraints, clinging to her as she walked Jacqueline over to a nearby couch; through her foggy vision she could see that the couple who was sitting there instantly vacated for the two of them, and she collapsed into the still-warm seat with a low groan.

  She heard Melissa ask someone to keep an eye on her while she went to get some water. Before Jacqueline even realized that Melissa was gone, she was already back. She sat down on the couch next to her and held her close, in an almost motherly fashion. “Hey there. You feeling alright?”

  “I… that was…” Jacqueline muttered.

  “It’s alright, just relax. I’ve got some water here if you need it.”

  “Thank you.”

  It was a strange feeling. Many of the stories and the BDSM guide books she’d read all mentioned aftercare. She knew that after an intense session, the bottom would need nurturing, that the top would need to guide them out of subspace and help bring them back into the world.

  Was what I felt subspace?

  Her mind and vision slowly cleared, and she realized how wet she’d gotten between her legs.

  “How are you feeling?” Melissa asked. “For a first timer, you did exceptionally well.”

  “I feel… tired. Like I just finished a very intense workout routine.” Jacqueline sipped her water, not realizing just how thirsty she’d been until after the first drops had passed between her lips. “It was incredible. Thank you.”

  Melissa smiled and softly combed her fingers through Jacqueline’s hair. She realized then just how close they had gotten; they were pretty much cuddling. When she was Jacob, she hardly ever got this close to Melissa, except when they hugged.

  “It’s strange,” Melissa said as she tucked some of Jacqueline’s blonde hair behind her ear. “You have this energy about you. It feels so familiar. Like, someone I know. I sensed it when we played. When a top and a bottom really connect, their energies mix and dance together.”

  Jacqueline took a long, slow drink of water. She wondered if she would have to somehow tell Melissa who she really was.

  “Maybe we met in some past life,” Jacqueline said.

  “Maybe,” Melissa replied.

  They remained that way for a while, even after Jacqueline had fully “sobered up”. She wondered if she would be incredibly sore when this was all over. If she’d wake up in her bed, in Jacob’s body, and his legs would kill him for all of the walking she had done in those wicked heels. She wondered if she would turn back at all.

  That wouldn’t be so bad, would it? she thought. Her mind played out the rest of her life as a woman in fast forward. But she shook the thought out of her head. There was no need to think about any of that right now. All that mattered was what was happening in the present.

  “Hey, so…” Melissa said, looking a little bit flustered. “I hope I’m not being too forward with this, but I was wondering…”

  “What?”

  Melissa glanced up at the clock on the wall. “The party will be over soon, and I really enjoyed our time together. I was wondering if maybe… you’d want to come back to my place?”

  Jacqueline smiled. Even in the dull lighting of the dungeon, she could see how red Melissa’s face had grown. She looked so shy, so innocent. It was funny seeing her this way when not too long ago she’d had the strong, confident, and seductive look of a dominatrix.

  “Yeah, I’d like that.” Jacqueline said.

  They stared at each other for what seemed like an eternity. Jacqueline felt herself drawn closer to Melissa. She closed her eyes and their lips met in a brief but passionate kiss, warm and soft and even better than Jacqueline could ever have imagined. Melissa broke it to stand and extend her hand; Jacqueline silently took it. She followed Melissa out of the club and into her car, not caring that she would be leaving her own behind.

  During the short trip back Melissa drove with one arm on the steering wheel and the other caressing the bare skin along Jacqueline’s upper inner thigh. No words were exchanged between the two women during the drive, just heated looks and giggles and from Jacqueline, soft moans.

  When the elevator doors closed behind them, Melissa pushed Jacqueline against the wall of the elevator and kissed her passionately, their tongues entwining as their hands eagerly roamed. Melissa fondled and squeezed the softness of Jacqueline’s breasts and ass while she clutched at Melissa’s shoulders in an attempt to keep from puddling onto the floor. Her dress was giving up its fight for modesty under Melissa’s welcome assault, rucking up around her waist and fishnet shifting to reveal her breasts beneath the cover of her coat, and she found she didn’t care.

  They were alone the entire way up, and their lips reluctantly parted as the elevator doors opened. With a wicked grin, Melissa wrapped her arm around Jacqueline’s waist and escorted her out of the carriage. The two women hastily made their way down the hallway to Melissa’s door, one clutching her coat tightly in an attempt to keep herself covered while the other tugged her eagerly along. The whole way up from the car, Jacqueline felt like a stranger. She felt as though she was in an alternate reality, that this wasn’t the same apartment complex that she also lived in, that this was a different building and hers was a world away.

  Even though she had been in Melissa’s apartment before—as Jacob—Jacqueline felt like this was her first time. She entered slowly, taking in the sight of Melissa’s geek chic decor. She felt a pair of hands reach up and slowly pull off the heavy coat that had been keeping her very revealing dress and exposed skin away from the prying eyes of the vanilla
world. Jacqueline blushed, tugging her hemline lower until it at least covered some of her bottom again.

  “Would you like something to drink?” Melissa asked as she walked past Jacqueline into her living room, tossing the coat over the back of a chair. Jacqueline knew that Melissa had a small bar in the corner of her living room, and that Melissa used to work as a bartender. She nodded her head in the direction of her bedroom. “Or would you prefer something else?”

  Jacqueline had never actually seen Melissa’s bedroom. Her bathroom was separate from the bedroom, which she had only been in a couple of times when she visited Melissa’s apartment. It was a simple bedroom with a queen-sized, four-poster bed. Melissa climbed onto the bed, and Jacqueline joined her without hesitation.

  They kissed again, their tongues writhing sensually as Melissa maneuvered Jacqueline onto her back and crawled over her. Melissa’s lips sensually explored the topography of her lover’s body, kiss after kiss caressing the curves of her cheek, the taut lines of her neck, the ridges of her collar, and the swell of her breasts. Jacqueline squirmed and moaned as Melissa’s clever lips moved, her fingers sliding their way up Jacqueline’s thighs until they vanished beneath the hemline of her dress.

  “Oh! Fuck!” Jacqueline gasped, and Melissa just grinned as her fingertips circled and teased the nub of Jacqueline’s new clit through the fabric of her underwear.

  But she didn’t stop there. “Let’s just get these out of the way,” Melissa giggled as her fingers slid up to hook under the waistband of Jacqueline’s thong. She opened her mouth to protest, as for a moment she worried that by removing the thong she’d turn back into a man, but before any words could escape her lips the thong was past her knees and already off one foot. The protest vanished when she remained a woman.

  “Oh my,” Melissa said, bringing the panties to her face and deeply inhaling Jacqueline’s warm scent. “Someone’s ripe for the plucking.” Jacqueline’s face went red as Melissa tossed the panties aside, embarrassed yet also incredibly turned on by the sight. Then Melissa looked at her closet and back out of her bedroom, brow furrowing as she thought of something. “You stay right there.”

 

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