D Is for Dress-Up

by Alison Tyler

  You toss the lingerie into the brush, leaving them for some lucky hiker to puzzle over. You smile up at me, your face and breasts moist with wine and melted chocolate, looking even more lascivious, somehow, than the skimpy lace did.

  “See?” you sigh. “I never should have let that lingerie salesgirl talk me into this. What have I been telling you? Chocolate and wine are filthy habits.” You snuggle up closer to me, our skins sliding together with the mixture of drink and debauchery.

  And when I kiss you, I taste them both. Sweet, like you, and just as forbidden.

  DomInaTeD DoLLY

  DOMINATED DOLLY. That’s what I was. Although I swear I never had the desire to wear women’s clothing until I met Mindy.

  I was a man’s man. Straight as an arrow. Not necessarily macho, but certainly a regular guy. Tall, fairly muscular. Not the easiest physique to explore transvestism, I suppose. But Mindy changed all that. Maybe it’s her fault I’m the way I am...or perhaps she simply unlocked a part of me I had kept hidden too long.

  I met her at the upscale department store makeup counter where she worked, and sparks flew instantaneously. I was ostensibly shopping for perfume for a woman I no longer cared about, and she sensed my plight immediately. We laughed effortlessly at each other’s jokes, and I was mesmerized by her energetic magnetism. Bright-red hair. Mintgreen eyes. Small breasts, shapely legs, and what appeared to be a perfect ass. A strong personality—assertive, aggressive, almost domineering.

  She encouraged me to stick around until her shift ended, promising to help me find the perfect gift for my (soon to be ex-) girlfriend. After she spritzed various scents on her wrists for me to admire, she gently rubbed up against me in her cotton floral sundress, and I was a goner.

  She took me home that night and, in the course of foreplay, playfully asked me to wear her panties. Eager to get laid, I obliged, somehow squeezing them over my sizeable thighs. My cock had never felt harder than it did with her undies encasing it. She teased me in a variety of ways for well over an hour, with my cock tucked into her silky prison.

  When we finally made love, my orgasm was surprisingly intense. Mindy credited her panties. I couldn’t argue.

  A few evenings later, after a quiet dinner followed by a short but wild night of dirty dancing at her favorite nightclub, she insisted that I don her thigh-high stockings after she eased them off. I made love to her that night wearing her nylons, and the silky feeling of my covered thighs against her bare body again brought me to one of my more powerful orgasms in memory.

  On subsequent occasions, she would blindfold me with her scarves—always silk, and in a variety of colors—and gag me securely with her bras and panties so I could taste the fabric she had just worn, along with her scent. She would brush against my naked flesh with cashmere sweaters, and the sensation would make me hard almost immediately. One night, she wore only a satin slip and insisted that I fuck her repeatedly without removing it. Total ecstasy.

  As weeks passed, I was in a constant state of arousal around her, never knowing what she was wearing or might make me wear. She was a merciless fabric prick-tease, and I felt powerless around her.

  One rainy Sunday afternoon in late fall, I nervously yet eagerly allowed her to handcuff me to her bedframe. She was still fully dressed from her shift at the makeup counter; I was already naked, my hard-on raging. She slipped off her shoes and peeled off her coffee-colored kneehighs. She then pulled one stocking over my throbbing cock, making sure the toe portion fit snuggly over the head of my dick.

  The sensation was absolutely maddening. She repeated the process with the second knee-high. I felt as though I were now wearing a nylon condom, yet my arousal built. She sat on my face and I licked her to several orgasms as my cock flopped around like some sort of silky fish. When she finally jerked me off, I soaked her stockings beyond belief.

  “Mindy...” I gasped.

  “Halloween is coming, Jason,” she said sternly, “and I want you to be my bitch.”

  I didn’t understand.

  “I want you to dress totally in drag for me. We’re going to a Halloween party as sisters. . .”

  The thought terrified yet intrigued me. “If that’s what you want, baby.”

  “That’s what I want, and it’s what you really want, too, isn’t it?”

  I couldn’t answer.

  The evening before Halloween was to be our dress rehearsal. I was instructed to leave my office as early as I could sneak away. Mindy was going to transform me to her total satisfaction. I was powerless to refuse or resist. She informed me that she had, over the course of a few errands, picked up a wardrobe in my approximate size, and I was to become “Jasmine.” I was ordered to get naked, and quickly complied.

  With a brand-new electric razor, Mindy proceeded to shave virtually all my visible body hair—chest, back, legs, underarms, even pubes. With a bit of help, I donned silky black Lycra panties that fit me better than any pair of hers, then sat silently as she began to fix my face. Blush, eye shadow, lipstick, various pencils—it was all a blur. A manicure and pedicure followed; bright-red nail polish soon covered my perfectly groomed fingernails and toenails. Mindy had put her years of counter experience to flawless use on me, and when she finally let me glance at my reflection, I was stunned at the “woman” I had become. I didn’t recognize myself. I actually felt feminine, despite the swollen hard-on hidden (barely) in my undies.

  “You almost look hot,” she said, giggling.

  Next came my wardrobe. A queen-sized pair of navy-blue pantyhose that I put on awkwardly while she watched. A large bra with padding already inserted. She hooked it for me, knowing I’d never be able to reach behind my back for such a maneuver. A silky ice-blue slip that glided sensually over my hairless body. A belted navy knee-length skirt that was just a bit tight at the waist, causing Mindy to playfully taunt me about my weight. A long-sleeved polyester white blouse that made me shiver when I put it on. Navy-blue pumps (size eleven!) to complete my ensemble. She had thought of everything.

  One final touch. “Wait here,” she commanded. She returned with what appeared to be a hatbox, and produced a fiery red wig that came dangerously close to matching her own hair color. She tugged it forcefully onto my scalp, clipping it in a couple of discreet places. Then she brushed it into a passable hairdo.

  “Well, honey, you’re just about done. Stand up and walk over to my mirror.”

  I nearly twisted an ankle in the pumps, walking awkwardly to obey her command. The visage that greeted me in the mirror was hysterical...frightening...funny...yet incredibly erotic, as well. My cock began to soften, to both my dismay and my relief.

  “This is who you really are, Jasmine,” Mindy said firmly. “This is not just your Halloween costume. This is who you’ll be for me, whenever I want you to. We’ll have to work on your voice, of course—and that walk has no grace at all—but you will learn.”

  “I’ll do anything for you, Mindy,” I replied. My hard-on once again strained against its nylon panty prison.

  “Yes, you will. Now go lie down on the bed for me, darling—face down.”

  I did as told. The silkiness of my panties, hose, and slip made me dizzy and lightheaded. I thought I might faint from the excitement of being totally made over. Something so wrong, so forbidden, yet it felt so completely right with Mindy.

  “Lift up your skirt, honey.” I did so to the best of my ability, and I felt Mindy firmly pulling down the waistband of my pantyhose, then my panties. As I turned slightly to try to assist her, I saw the strap-on black dildo that sprang like a black rubber panther from her crotch.

  My cock, already swollen and throbbing, again sprang to rock-hard status.

  I truly was about to become Mindy’s bitch and couldn’t imagine resisting. As it turned out, I came quickly and explosively, just seconds before she did. And I knew there would be more days and nights of dressing up ahead.

  THe MYsTeRIous AFFaIR aT STYLes

  DAVID THOUGHT IT WAS LIKE every Agath
a Christie novel he’d ever read.

  Lazy rain lashed the night-blackened windows. Only candles and the ghost of a fading fire lit the drawing room. The guests (or suspects, as David now thought of them) lounged on settees and convenient chairs. They sipped at cocktail glasses, smoked cigarettes through elegant tortoiseshell holders, and exchanged an idle banter of shallow pleasantries.

  David stood before the fire and stared at the five women. “The culprit is one of you ladies,” he declared. “And I think I’ve finally worked out which one it is.”

  Eyebrows arched.

  Speculative glances were tossed in his direction.

  Lavinia giggled as she splashed cognac from a decanter into a balloon glass. “Culprit, Davy?” Her voice was slurred from one tipple too many. “Who’s been culpritting?”

  “Yeah,” Sonia agreed. “What are we supposed to have done, David?”

  All five women regarded him with polite expectation. A fug of tobacco smoke hung in the air. Staring at them in their costumes for the themed ’20s weekend, he thought it was like looking at a nicotinetinted photograph from days gone by. The combined weight of their cool appraisals made him want to squirm. But he remained stalwart and steadfast.

  Mousy, blonde Talia, anxious as always: “What have we done, David?”

  “Fess up, Davy.” This was Maria, confident to the point of arrogance. In her typically confrontational manner she asked, “What’s the charge?”

  Only Olivia said nothing.

  David wondered whether her silence implied something. Or whether he was merely clutching at straws in his bid to discover the guilty party. Did Olivia say nothing because she feared he might recognize an inflection in her voice? Or was she naturally taciturn? He racked his brains, trying to remember any conversation he’d had with her since the weekend began. As the silence dragged on, and the five women continued to stare at him, he realized he would have to think about the matter later. For now he needed to supply an answer to their question.

  “Last night I was accosted,” David began gruffly.

  It was a fact.

  But it was also one hell of an understatement.

  The last to leave the drawing room, after turning off the lights and ensuring that the fire was dying he stepped into the darkened hall. A woman’s body pressed close to his. Feminine fingers slipped against his cheek and then went to the back of his skull. More fingers slipped to his waist and trailed down to his groin.

  The hand at his groin caressed him intimately.

  Through the fabric of his trousers, inquisitive fingertips traced the shape of his length. Before he could draw a startled breath, his head was pulled against a pair of soft, yielding lips. A tongue plundered his mouth as the hand at his loins stroked him to hardness. Plump breasts pushed against his chest. The scent of a deliciously floral perfume filled his nostrils. His initial panic subsided and excitement flooded his body. A long, coltish leg rubbed against the outside of his thigh. The kiss lingered for a glorious age. And, beneath the floral scent, he caught the musk of feminine excitement.

  His hands reached for her breasts. He found their shape and noted that they were large enough to fill his palms. A thin layer of silk covered them and he caught the sensation of stiff nipples brushing through the gossamer fabric and touching his fingers.

  He held her briefly, savoring the kiss, the caress, the contact.

  And then she pulled his hair.

  “Accosted?”

  “What does that mean?”

  “Who accosted you, Davy?”

  “If he knew who accosted him, Talia, he wouldn’t have summoned us here, would he?” Maria glowered at the meek blonde.

  Again, Olivia said nothing. She regarded him from behind fluttering eyelashes. Long dark curls framed her pale, elfin face. Like the rest of the guests (or suspects), she was dressed in a fashionable ensemble. Olivia’s costume emphasized her full breasts and narrow waist. Her expression was enigmatic, beguiling, and perplexing. She certainly had a build that matched that of the woman he had encountered the previous night. But David knew the same thing could be said for the rest of them.

  “What happened, David?” Sonia wasn’t always the first to ask questions, but with Lavinia giggling drunkenly he supposed she had become the group’s spokeswoman. “Tell us all about it,” Sonia encouraged.

  He blushed.

  The memory was enough to make his temperature soar.

  The woman pulled his hair. He was so startled that he immediately released his hold on her breasts. The hand at his groin tightened. Manicured nails pressed into the pulsing heat of his shaft. Separate pains in his scalp and his erection vied for his attention. The contrast between the excitement of the kiss and the agony of those torments was shocking.

  “Never touch me without permission,” she hissed. “Never!”

  He tried to place her voice and couldn’t.

  He knew each of the women sharing the house for the weekend. But he had never heard any of them hiss with such passion and ferocity. The anger and power in her tone were deafening, even though they were no louder than a sigh.

  “You don’t touch me, David,” she growled. “Not without my permission. Do you understand, you little worm? Is that clear, you worthless maggot?”

  As she spat her muted questions, she gripped him tighter. Her hold on his hair was hard enough to drag strands from their follicles. But that was the least-worrisome aspect of the torment. Her grip around his length was an agony. He worried that her fingers were plunging through the fabric of his trousers and burrowing into the soft flesh of his shaft. He fretted that she was tearing him, scarring him, preparing to maim him forever.

  Perversely, those fears made his arousal throb with greater intensity.

  “Do you understand, Davy?”

  “I understand,” he gasped.

  She released her hold on his head.

  The hand around his erection loosened but never moved away.

  “That was an improper way for someone to handle a young lady,” she said quietly.

  Her whispered voice was maddeningly familiar. He knew her. He recognized her. But it was impossible to connect the name or face that belonged to the blackened silhouette holding him and heightening his excitement.

  “A very improper way to handle a young lady,” she said again. “And I think you should apologize now.”

  “I’m sorry,” he stammered. He kept his voice down to the same apologetic hush where hers resided. Panic and disorientation had convinced him that he didn’t want the rest of the household to be disturbed and come downstairs to find him involved with one of the guests. All that mattered was appeasing the unstable woman who had surprised him in the main hall. “I’m so dreadfully sorry.”

  “I want more than words,” she breathed. Her hand moved back to his head and he was pushed to his knees. The polished surface of the hardwood floor resounded with a solid thud. From above he heard her whisper, “I want a lot more than words.” She stepped forward and he caught the game fragrance of her wet sex. “Come on, Davy. You know that actions speak louder than words.”

  “I don’t think I need to go into the details,” David blustered. “It’s enough to say I was accosted by an unknown assailant.”

  Sonia inquired, “Did they hurt you?”

  Sobering up quickly, Lavinia asked, “Did they take anything?”

  “Who was it?” Talia asked.

  Maria rolled her eyes and glared at the blonde. “Which part of ‘unknown’ confused you? He just said he was accosted by an unknown assailant. That means he doesn’t know who it was.” She glanced at David and said, “What makes you think it was one of us?”

  He considered Maria for a moment. She was supremely confident and seemed to take pleasure from cruelly dominating Talia. Wasn’t he looking for a woman who was able to dominate others in that manner? Didn’t she fit the description perfectly? The woman in the hall had certainly enjoyed dominating, and her propensity for cruelty had known no bounds.
/>   “Don’t even think of kissing that until you’ve had my permission.”

  He held his breath.

  It hadn’t crossed his mind to consider doing as she implied. He wasn’t even sure what she meant. The hall was dark but his eyes had begun to adjust to the lack of light. He could make out the faint glow of alabaster thighs and the dark bands of stocking tops. As he tried to focus his gaze on the shifting shadows, he puzzled over the dark triangle at the top of the thighs. It was only when he drew another breath that he realized his face was mere inches from the woman’s bare pussy. He almost staggered back in shock.

  “You may start by kissing my feet.”

  “What?”

  “Don’t ask questions, maggot. Just grovel before my feet and put your lips against my toes.”

  He considered refusing, but the thought lasted no longer than an instant. He didn’t know who she was, but he relished the control she had over him. Lowering his mouth to one foot, finding the shape with his fingers then guiding his lips to her stocking-sheathed toes, he kissed it, then the other.

  “Good boy,” she murmured. “You can be obedient, can’t you, Davy?”

  “Davy?”

  Maria’s voice snatched him from his thoughts.

  “What makes you think it was one of us?” she asked again.

  He shook his head to clear his mind of the constant distractions. “It happened in the hall last night,” he explained. “Aside from the six of us, there was no one else here at Styles. Four of you ladies had retired. One of you ambushed me after I’d finished securing the house for the evening.”

  “Ambushed?” Lavinia was giggling again. “What on earth are you talking about, Davy? You make it sound like a troop of commandos took you down at gunpoint.”

  David glared at her.

  “Yeah,” Sonia agreed. “You’re not telling us much, David. What actually did happen?”

  His cheeks turned crimson.

  “You may kiss me higher.”

  He moved his mouth from her toes to her shins. The silk-covered flesh was salted with her fragrance. The flavor was divine against his lips. Raising his kisses higher, reaching her knees and then her thighs, he could feel the pulse of his arousal throb with renewed urgency. The scent of her pussy sweetened every breath. Even though he had yet to touch her sex, he felt as though he had drunk every droplet of moisture from within her hole just by breathing.