D Is for Dress-Up

by Alison Tyler

  “Is this getting you excited?”

  “Yes.”

  “Really excited?”

  “Christ! Yes!”

  “Then I shall permit you to masturbate.”

  It was a formal way of speaking, and made him immediately discount Sonia and Maria as potential suspects. They spoke in a fashion more prone to profanities and vulgarities. Either of those women would have told him to wank or tug off—not masturbate. As he fumbled for the zip at the front of his trousers, he considered that the woman dominating him might be assuming a role, and therefore curtailing her normal mode of speech. The assumptions and theories tumbled through his mind, reinforcing the knowledge that she could be anyone.

  But as soon as the heat of his erection lay across his palm, David was no longer thinking about who she might be, only that she had to be obeyed.

  “Masturbate while you kiss my pussy,” she insisted. “But you can’t ejaculate until I give permission. Do you understand that, maggot?”

  David sighed.

  David sighed. He drew a deep breath and said, “As I was securing the building last night, one of you ladies surprised me in the main hall.’’

  “I suppose it’s better than being startled up the back passage,” Lavinia quipped. She chuckled at her own ribald humor.

  David glared at her, wondering what she knew about the incident. It was almost as though she was taunting him with her secret knowledge of all that had occurred.

  “Tongue it deeper.”

  Her hand was back on his head. She pulled his hair, guiding him this way and that, forcing his neck back so his tongue could more easily slide into the velvety, wet confines of her sex. His nose was daubed with the residue of her musk, and every breath was colored with her scent. No longer spluttering for air, simply doing as she demanded regardless of whether he was allowed to breathe, David pushed his tongue inside and willed the woman to climax. Her pussy lips kissed his mouth and smothered his nose. The slick flesh drew wetly against him.

  His hand no longer rolled back and forth along his penis. Her domination left him weak with the desire to come, and he didn’t dare stroke his cock for fear of a premature climax. Whoever she was—and his mind was still trying to find an answer to that particular puzzle—she would be egregiously unhappy if he ejaculated without permission. And, considering that she had already treated him with so much cruelty and disdain, David didn’t want to do anything that would incur her greater wrath.

  “That’s it, you maggot,” she growled. Her tone was heavy with arousal. Each word was dragged from her chest on a wave of mounting excitement. She yanked at his scalp as though she had forgotten that her fingers clutched fistfuls of his hair. “That’s it, worm. Tongue fuck me deeper: deeper.”

  He almost came. Her orgasm was so powerful that the radiating waves came close to carrying him with them. She pressed his face hard against her pelvis and bucked her hips forward and into his nose. The sensation of being controlled was so powerful that he had to invest every effort into staving off his climax. He wouldn’t allow himself to even think about the spray of musk she spurted into his face.

  She was panting as she lowered herself down to his side. In her state of breathlessness he could almost work out which of the guests she was.

  “You didn’t come, did you?”

  “No.”

  “Are you sure?” she pressed. “Should I taste your cock and see if you’re telling the truth?”

  She didn’t wait for his response. From the darkness he felt silken lips engulf his shaft. A sensuous tongue traced the shape of his glans and then trailed along his length. The frisson of excitement was so strong it was unbearable, but David valiantly refused to let the climax sweep through him. If he came without her permission, she would make him suffer. If he erupted in her mouth, he imagined that her cruelty would reach an unimaginable extreme.

  “What an obedient maggot you are,” she cooed. “I think you should have a special treat for doing as you’re told.”

  He hadn’t noticed that her lips were no longer encircling his cock. The sensation had been so divine that it had continued without the need for her mouth around his dick. He clenched every muscle in his body, hoping the effort would be enough to stanch the inevitable pulse of his orgasm.

  “Stay on your knees, Davy,” she told him. “But pull your pants down and show me your arsehole. I want to slide a finger inside your back passage.”

  “Do you know what happened last night, Lavinia?”

  “Only what you’ve told us so far,” Lavinia replied cheerfully. “And that’s not much, is it Davy?”

  He scowled, sure that she knew more than she was letting on, but reluctant to press the point. Before he could decide how best to handle the situation, Maria was calling to him from across the room.

  “Lavinia has a point, David. This doesn’t concern her, and it certainly doesn’t concern me. I’m going for an early night.”

  He wanted to protest and say that he hadn’t finished his interrogation yet. But, as he watched, each of the five women nodded agreement and pulled herself from her seat. He watched them file past him toward the doorway. Maria opened it wide and David caught a brief glimpse of the small area of the main hall where he had suffered his final humiliation.

  “How does that feel, Davy? How do you like having two fingers up your ass?”

  “Good,” he grunted. “Very good.”

  “Stroke yourself. Don’t come. But stroke yourself faster.”

  He was loathe to obey the instruction. She had forbidden him to climax until she gave permission. If he stroked faster, he knew the orgasm would be torn from his swollen dick. He assumed that there would be a simple solution to the dilemma if she allowed him a moment to think about it. But because her face was close to his, and because she had ingratiated a pair of slender fingers into his anus, it was impossible to channel his thoughts in that direction. Obligingly he rolled his fist up and down his shaft.

  “You really do have a tight little ass, Davy. How would like me to wear a strap-on and ride you up there like the little bitch that you are?”

  He whimpered. The words were strong enough to push him to the brink of climax. The thought that she might do as she threatened made him struggle to maintain control. He felt sure the orgasm was going to burst from him at any second.

  “Do you think I can slip a third finger up there?”

  “No.” He said it too quickly, too sharply. Worried she might take offense, he said more soothingly, “I don’t think I could... I mean...”

  “You better be able to take it, Davy,” she murmured. “And remember: I won’t be happy if you come without my permission.”

  There was no opportunity for argument. Before David could catch his breath, the muscle of his sphincter was stretched. She had pulled her hand away from his rear—not taking the fingers out but allowing them to linger on the verge of exiting the muscle—and he was almost convulsed by the climactic thrill his body needed. His scrotum was a tight sac that would explode at any second. And his anus was widened to a fresh and unbearable width. “Stop stroking,” she snapped.

  He obeyed instantly. His hand moved away from his cock and he simply suffered the indignity of being impaled on her fingers. His hands clawed against the polished wooden floor. Sweat clung to his brow and palpitations racked his body. In the darkness, he saw himself suspended over the precipice of a grand and unending chasm of orgasm.

  “Let me stroke that cock for you,” she whispered.

  Her soft fingers encircled him.

  In contrast to the harsh treatment at his anus, her touch was light and sensuous on his erection as she stroked with a gentle rhythm. At the same time she buried her fingers deeper into his backside. The different extremes she provided—pleasure at his cock, and pain at his anus—propelled him quickly to the point of no return.

  “Let me stroke you,” she breathed. “But don’t you dare come until I’ve given you permission.”

  Certain he couldn�
��t obey, David groaned.

  And with that sound the first convulsions of his climax were ripped from him. The orgasm was powerful enough to be an agony. His rectum gripped hard around her fingers. His cock shuddered and convulsed with the strength of his explosion. His shaft pulsed repeatedly, spraying globules of semen into the darkness. He heard them spatter against the polished floor. The sensation of release was the euphoria he had expected. But, as awareness came back to him, David understood that he had upset the woman who still held his cock and continued to keep her fingers pushed into his ass.

  She withdrew from him with obvious disdain.

  His butt was left feeling hollow.

  His cock felt sore and spent and almost bruised.

  “I’m sorry.”

  “You disobeyed my instruction.”

  “I’m so very sorry.”

  She pulled herself away from him and, although he could see nothing in the darkness, he knew she was towering over him. “Lick it up, Davy,” she hissed. “Lick up the mess you’ve made and then go to bed.”

  Without any thought of disobedience, David did as asked. He worked blindly in the dark, thrusting his face against the polished wood. The taste was obscene. His movements were hurried and frenzied, for he felt desperate to do as he had been instructed in the hopes that he could appease the glorious, unknown tyrant who had pleasured him so intensely.

  Yet, when he had finished, David realized she had left him alone in the hall. If not for the aching in his balls, the punished sensation in his rear, and the phlegmatic remnants in his mouth, she might never have been there. He returned to the main room and retrieved a candle so that he could make sure that his cleaning operation had been complete. Although he was anxious to know who she was, he wanted to make sure that all evidence of their encounter had been removed before he retired for the night.

  The room continued to look like something created by Agatha Christie, but now it was after the final act and all the characters had left. Deserted, the room made him feel as though he had failed. He would never know the identity of his mystery assailant, and that meant he would never experience her domination again. Frustration and annoyance made his smile bitter and he went to the brandy decanter and poured a balloon glass half full.

  He supposed he hadn’t wanted to discover whodunit.

  He just wanted to know if they could do it again.

  Swallowing quickly as the brandy burnt his throat, he paused and listened. Although he couldn’t be sure, he thought he had heard a footstep on the polished floor of the main hall. Draining the remainder of the contents in one swig, he carefully went through the process of extinguishing all the candles and putting out the flames in the fireplace. And as he left the room, for the first time since the evening had begun, David’s smile was filled with hope.

  SmoKInG In THe BoYS’ Room

  DON’T SIT DOWN,” I SNAPPED. Michelle stood nervously in front of the desk, popping her gum and shifting from side to side. She was dressed for the occasion: short, tight plaid skirt decent by only a couple of inches; white stockings; high-heeled shoes; loose white blouse with just a hint of her white, lacy bra showing where she’d carelessly let a button or two come undone. Her blonde hair was in pigtails and she was wearing heavy eye-liner and lipstick. My twenty-eight-year-old girlfriend was dressed up in the height of Catholic schoolgirl drag, pretending to be the naughty slut she’d always wanted to be, the slut she’d begged me to let her become for an evening—and I planned to comply, eagerly.

  I regarded her from behind the big desk, tapping the eighteen-inch ruler on my palm.

  “Miss Peabody informs me that you were caught smoking. Is this true?”

  “Honest, sir! I wasn’t smoking, honest I wasn’t!”

  I stood up, moving quickly. Michelle took a step back and I snapped, “Stay still!”

  I came close to her, bending down so my face was just inches from hers. I grabbed a pigtail and sniffed it. It reeked of smoke—ten points for realism.

  “Not only smoking, but lying,” I growled.

  Michelle exclaimed: “The other girls were smoking, but honest, I wasn’t!”

  I bent closer to her face, sniffing.

  “You weren’t smoking? You swear?”

  She shook her head quickly.

  I put out my hand. “Spit out your gum, Michelle.”

  Nervously, she leaned over and let her bubblegum fall into my hand.

  She looked into my eyes, fear crossing her face as I came close. Suddenly I grabbed the back of her head and pressed my mouth to hers, forcing my tongue between her lips as she whimpered and tried to pull away. I held her fast, probing her mouth with my tongue and tasting the telltale residue of tobacco: sharp, rich, nasty.

  I pulled back and stared at her. Michelle’s red lipstick was smeared across her mouth. I wiped my lips on one of her blonde pigtails and saw its tip rouge faintly red.

  “Your excuses fall apart under investigation, Michelle. I recommend that you start telling the truth.” I sat on the edge of the desk and tapped the ruler on my palm.

  Michelle blushed fiercely and looked down at the floor in humiliation. Her pigtails hung past her shoulders; just underneath them, the telltale peaks of her nipples had begun to stand out quite plainly under the blouse.

  “You know the punishment for smoking, Michelle.’’

  She nodded. “Yes, sir,” she said miserably.

  “If you’d like, you could encourage me to lessen the punishment a bit. Say, by telling me who gave you the cigarettes?”

  She looked up at me, her blue eyes wide and bright. “Sir?”

  I took her chin between my thumb and forefinger and held her fast while she tried to look away. “Who gave you the cigarettes, Michelle? You know full well that you can’t have bought them—you’re not old enough. Now, who gave them to you?”

  Michelle stared into my face, putting on a beautiful show of being too scared to talk. I could already feel my cock hardening in my pants, and Michelle’s nipples were more evident than ever under the blouse.

  “Miss Peabody said you were smoking in the boys’ room. Is it one of the boys who gave you the cigarettes? Andy Taylor?”

  “I—I—I,” she began.

  “Your parents already told me in our parent—teacher conference that they cut off your allowance because they caught you drinking. So you couldn’t have given Andy money for the cigarettes. What did you give him, Michelle?”

  Michelle was a gorgeous actress. She looked on the verge of tears. “I thought so,” I said. “You sucked him with that pert little mouth of yours, didn’t you, Michelle? He smeared your lipstick all over that pretty face, didn’t he?”

  Shifting nervously, Michelle nodded.

  “Uh-huh,” she said.

  “Did he have you service his friends, too, Michelle?”

  “Just a few of them,” she whimpered pathetically. Her nipples were now even more clearly evident.

  “How many?” I asked sternly.

  “S... six or eight,” she said.

  “You’re sure? Not more?”

  “Well, maybe ten,” she whispered.

  “Ten boys, all using that mouth of yours, just for a few cigarettes. Tsk-tsk, Michelle. Don’t you know that even whores your age get cash? What have you got to say for yourself?”

  “I—I don’t know,” she said.

  “Open your blouse,” I told her.

  “Sir?”

  “I said unbutton your blouse, Michelle. Right now.”

  Michelle began to fidget with her top button, looking at me for reassurance.

  I tapped the ruler on my palm. “Go ahead,” I told her.

  She unbuttoned her blouse slowly, letting it fall open to reveal the creamy mounds of her breasts imprisoned in their too-tight, too-lowcut bra. Her nipples peeked out quite clearly. Tucked into her cleavage was a cigarette.

  “I thought so,” I said. “Give it to me.”

  She took the slightly crushed cigarette out of her cleavage
and handed it to me.

  “Anywhere else you’re hiding the cigarettes your boyfriends gave you, Michelle?”

  She shook her head.

  “We’ll see. Lift your skirt.”

  “Please,” she said, tears forming in her eyes. “Please don’t make me...”

  “Lift your skirt, Michelle. Right now.”

  She took hold of her tight skirt and snugged it up over her thighs, revealing the lace tops of her stockings where they hitched to her garters.

  “Higher,” I said.

  She lifted her skirt up over her crotch, revealing smooth-shaved pussy unhindered by panties. Tucked between her thighs, in the top of her stockings, was a pack of Marlboros with matches in the cellophane.

  “I thought so. Give them to me.”

  She took out the pack of cigarettes and handed them to me. I took them and got one out, lighting it while she watched.

  I took a drag and blew smoke at her.

  “Would you like one?”

  She shook her head nervously.

  “I’ll bet you would, but you’re too ashamed to ask for one. Now, Michelle, care to tell me why you’re not wearing any panties?”

  “He... he doesn’t like me to,” she said.

  “Andy?”

  She nodded.

  “Does he like you to shave your pussy, too?”

  “N… no,” she said. “That was my idea.”

  “I’m sure it was. Do you like the way it feels?”

  She nodded.

  “You do realize that only strippers and prostitutes shave down there, don’t you?”

  She shook her head.

  “Well, they do. Which are you, Michelle?”

  She looked at me dumbly. I blew smoke in her face.

  “You’re a whore. At least, that’s what your clothing tells me.” “Please, sir... I’ll try to be good.”