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2023-07-20
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Mr. Wooster's Sudden Appearance in Women's Apparel

Summary:

Jeeves is out enjoying his night off when he suddenly runs into - literally - Mr. Wooster dressed in women's clothing and pursued by police. To escape they turn to the old ploy: pretend to be kissing (and worse) so the pursuers will not recognize Bertie.

Notes:

The Masquerade Laws I refer to in this fic were real, were used to oppress gay and gender nonconforming people in the 1920s, and they were one of the reasons why the Stonewall Riot broke out some decades later. There's a good summary here: https://www.history.com/news/stonewall-riots-lgbtq-drag-three-article-rule

 

Also: This is obviously a very trope-y fic. I was feeling stuck and I wanted to push myself to write every day, if only for practice, so I made a little analogue prompt generator where I randomly chose one fandom and one trope to combine into a story. This is one of those stories.

Prompt generator: Jeeves&Wooster, fuck or die (or in this case, pretend to fuck or be arrested)

Work Text:

The life of a valet in a bright, young gentleman's employ is rarely a sedentary one. I had been with my employer, Mr. Wooster, for more than two years when we undertook a voyage to New York in the spring. This was not our first trip to that great city, and I had made all the necessary arrangements to ensure our flat would be ready for our arrival. In the two years I had been with him, I had learned enough of Mr. Wooster's tastes and peculiarities to know exactly how to stock the pantry, which tradesmen to call in, and what troubles to expect. I had even begun contemplating his American acquaintances during our crossing, sorting them in my mind into more and less probable to present a challenge. I had ordered the piano tuned and brought several packets of good tea in our luggage. I was looking forward to an enjoyable stay.

Of course, Mr. Wooster himself made any journey enjoyable. During our first two years together, I had not only become well acquainted with his habits; I had also come to know his heart, mind and soul. I was entranced from the first moment of our acquaintance. At first, I was fascinated by his uncanny habit of finding trouble wherever he went. At times, it was not even through any fault of his own; trouble simply seemed to follow and find him. This presented several challenges to my intellect when he wished me to help him, which I enjoyed immensely. Over time, I also found myself charmed by his good humour, his optimism, his boyish good looks and his generosity. Within a year, I was so charmed by my young employer that I could not deny to myself that I loved him.

Mr. Wooster thankfully seemed oblivious to my admiration. It is one thing to be an invert, another yet to belong to a different social class; my serious nature and plain looks could not further me in his estimation, either. I harboured no hopes for reciprocation, but I found my existence in his household a comfortable and rewarding one nonetheless. In short, I was content to love my employer from my position as his valet, enjoy his generosity and open admiration for my abilities, and occasionally relieve my longing for him in the privacy of my own chambers with the aid of my own hand.

And so, I followed him to New York, saw to his every comfort on the journey, and had us both settled into the flat and going about our business as usual. Then, one spring night in New York, everything changed between us.

Mister Wooster had gone out for the evening, informing me that he would be very late in returning, and had given me the night off from my duties, as well as insisted I take a few drinks at his expense. I appreciated his generosity in this, but I was not in a sociable mood, and so I had decided to stroll along the streets of Manhattan in solitude instead. I was walking in the clement spring night, contemplating where I might wish to take my annual holiday in a few months, when I heard a great commotion. Shrill police whistles split the quiet darkness, and shouts sounded in the distance.

I stopped and looked around to see if I could determine the source of the commotion. American police are rather more excitable than our British officers, and I thought perhaps they were raiding a speak-easy; something which never fails to rouse their spirits. I heard running footsteps, and clearly from a woman's shoes – the clicks of heels came rapidly and steadily. A person came running around a corner, headed straight for me, and collided with me as they turned to look behind them while still running.

For a moment, we grappled – I to keep us both upright, and the other person to free themselves of my grasp. I heard another police whistle, and then the person stopped and looked up into my eyes – and I recognised my employer. It was Mr. Wooster, but even as I recognised him, I also noticed what he was wearing: women's attire. He was dressed in evening gown, heeled shoes, a shawl, jewels, and a silk turban; he even had his face painted like a woman.

“Sir,” I gasped, and in that moment, he recognised me, too.

“Oh, God,” he whispered, clearly stricken, but just then we heard the shouts of police approaching.

“Help me,” he breathed, looking around like a hunted animal. “I'll give you anything, Jeeves, pay you every last shilling I own if you'll help me!”

I noticed a narrow alley just ahead of us, and pulled Mr. Wooster with me into that dark space. We moved further into the alley, but it dead-ended in a brick wall, and I turned to look him in the eyes again. His eyes were shaded in dark blue and lined in black, and his lashes were longer, darker and fuller than they had ever been. The sight shocked me to my core.

“Sir, do they know who you are?” I whispered, keeping my voice low.

He shook his head, and lowered his gaze. “I never registered in the club book,” he said, and his lips – dark red and heart-shaped – barely moved as he spoke. “But they heard me talk. They know I'm not a woman.”

For half a second, I despaired. A foreigner caught drinking alcohol in a nightclub would be fined and sent on his way; nothing Mr. Wooster had not experienced before. But a man wearing women's clothing and face paints in public? One who was clearly not an entertainer in a licensed nightclub? Men and women who broke the Masquerade Laws were frequently jailed for far less. If they were lucky, they were not subjected to excessive violence from the police underway.

Of course, if we were caught in what I planned to do, the punishment for us both would be far harsher than what Mr. Wooster could expect from his apparel. If I did nothing, he would be arrested for breaking one set of laws; if my plan did not work, we would both be gaoled for breaking another, and Mr. Wooster's entire future ruined. It was not a fortifying thought. But the terror in his eyes swayed me, and I made my decision.

“Pretend you are a woman,” I told him softly as I heard the sounds of angry police officers come closer. “Say nothing, and take your direction from me. Trust me, sir.”

He nodded, wild-eyed and white-faced beneath his paints. I took hold of him, swung him around until his back was against the brick wall at the end of the alley, and I pressed him into it. I hurriedly loosened my trousers, unbuttoning my braces and pushing them down around my knees, taking my underclothes with them. Mr. Wooster gaped at me, but said nothing. I reached down and grasped his leg, and he let me lift it. He wore stockings, but even through them I could feel it – his legs were shaven. He was smooth as silk. I bit back a groan even as I pressed our bodies together, one of his legs up around my hip.

“Hey, look,” someone said behind me, as if to a companion, and I began thrusting against Mr. Wooster. His dress, rucked up around his hips, provided no protection from the heat of him as I pretended I was taking him there against that rough wall.

He drew in a sharp breath, and the sound hissed against my skin. I leaned in and smeared my cheek along his lips, desperately hoping this detail would add verisimilitude to our subterfuge. I let my hips jerk against his all the while, desperately hoping to save us both rather than condemn us.

“Hey, pal, whatcha doing?” a coarse voice called from the direction of the street.

“Gettin' what I paid for,” I grunted back, trying my best at an American accent. “Took her out to dinner, didn't I?”

I saw light on the wall around us, and I knew they were using a flash light. I turned my face slightly to the side to display the smear of red lipstick on my cheek. I prayed they would see only what I had arranged for them to see: a man, trousers around his knees, with a woman's legs wrapped around him at the back of an alley. I sent silent thanks to my employer for being so thorough with his disguise; his leg looked, unless one stared too long, entirely feminine. I was in my brown tweed and so would not attract more attention than necessary; a morning coat would have seemed far more suspicious.

There was an uncouth chuckle. “Yeah, okay. Keep it down, wouldya?”

And then I heard them moving away.

I stopped thrusting my hips against Mr. Wooster's. I held still, perfectly still, for long moments. Mr. Wooster was trembling against me, but he didn't make a sound. Behind me, I could hear the sounds of police moving through the streets, then away, and finally, there was quiet. I looked into Mr. Wooster's eyes. With his heeled shoes, he was as tall as me, but he was pressed back against the wall and balancing on one leg, the other leg still around my hip, so I still looked slightly down to meet his gaze.

“Jeeves,” he breathed, staring at me.

That was when I felt his hardness against my own manhood.

I looked down. He was wearing a type of underclothing I had never seen before, clearly constructed to disguise certain shapes below the waist. And yet, I could feel the heat and hardness of him straining against the material. When I looked back up, meeting his eyes, I felt desire warm my skin. He was so beautiful.

“Sir,” I murmured softly. “Are you injured?”

“No,” he whispered, then put both hands on my shoulders. “Jeeves, don't stop.”

He wanted me to pleasure him. His leg trembled in my grip. I felt light-headed with lust, but I exercised self-control and focused on what was most pressing. “Sir, we should go. You need to return to the flat to remove your... disguise.”

His eyes shuttered and he drew back, lust draining out of his visage. He looked away, shamefaced. “What must you think of me, Jeeves.”

“I will see you safe back in our flat first, sir,” I insisted, and gently let his leg down. He nearly stumbled when he attempted to put weight on it, and I held him up. I returned myself to decency as quickly as I could, and helped him straighten his turban and jewels.

Once I judged it safe, we wrapped him in the shawl so that his face was barely visible, and hurried around the corner. We moved quickly and quietly through the night. Barely twenty minutes later, we were at our building. There was no elevator operator on duty during the night, but our nights watchman stared at us as we hurried through the lobby. I tipped him handsomely and winked at him, hoping to give him the impression that I was bringing home a lady while my employer was out.

He grinned and took the tip without comment.

Mr. Wooster had not spoken since we left the alley, and he did not speak again until we were both inside the flat and the door was locked behind us. He quietly let his shawl fall to the floor, then strode for the sideboard and took up a bottle of brandy. He splashed an unseemly amount into a glass and set it to his lips, drained the entire glass, and repeated the procedure. Only then did he turn to look at me.

“What should I... How much should I make it out to, Jeeves?” he asked, voice hoarse.

“Sir?” I asked, not quite able to follow him.

He waved his glass around. “The cheque, Jeeves. The bank note. What will you take for rescuing me from the police and taking this night with you to the grave?”

I understood how afraid he must be – I knew it with the fear of the invert whose every romantic dalliance carries with it a threat of imprisonment. And yet, it felt insulting for him to offer me money. Had I not always come to his aid when he needed me? Did I not soothe and command his life at every turn when necessary? Would I not do this, and every other unthinkable thing, to ensure his well-being?

“I will take my usual salary, sir,” I said coldly, “when it is due.”

He stared at me. He was still made up and dressed like a woman, and the sight filled me with longing, unease, and wonder in equal measure.

“You... You're staying on?” he asked, sounding so very surprised.

“Unless you intend to dismiss me, sir, yes,” I said quickly. He might yet find me too great a risk and give me notice, and the thought was agony.

“You find the young master in... in this,” he persisted, gesturing to his appearance, “running from police, forcing you to... that thing in the alley – and you're staying?”

I did my best to look calm and steady. “I was not forced, sir. You asked for my help and I gave it. Yes, sir, I should prefer to remain in your employ.”

Mr. Wooster slowly took his turban off, then the jewellery, placing the pieces inside the silk. In the electric lights of our flat, I could see the jewellery was only paste, but impressive, nonetheless. He sat on the sofa to remove his heels, too, and I was strongly reminded of the softness of his leg under my hand. I smothered a groan again.

“I don't know what to say, Jeeves.”

I picked up his shawl, then approached him slowly. “Will you need my assistance on similar matters in future, sir?”

He grimaced. “I don't think I can bring myself to go out like this again. The other chap... I think they hurt him. Badly.”

“If I might make the suggestion, sir,” I said, folding the shawl and placing it on the table next to his turban. “If you were to inform me beforehand, I might be better placed to assist you in making good your escape next time.”

He shook his head. “This was all wrong, Jeeves. Nobody was supposed to be hurt. We didn't think they would raid the club tonight. I... I only wanted to feel pretty.”

He blushed furiously and looked away.

Longing twisted through me at his words. “You are, sir. You look beautiful.”

His head snapped up. He looked up at me with painted eyes full of pain. “Jeeves?”

“You asked me, in the alley,” I said, and I knew I could be bold – he had given me, although unwittingly, everything that made him vulnerable. There was no need to hide what I was from him, not after that night. “You asked for more. Sir.”

I could see that he remembered, and he was ashamed. I held a hand out to him. “Do you want me to not stop now?”

Mr. Wooster's mouth fell open, and those painted red lips were gloriously tempting.

“Sir?”

“Jeeves, do you... would you come to bed with me?” he asked, and he sounded so utterly bewildered that I needed to reassure him.

“You are beautiful, sir, in costume or out of it. I have always thought so,” I said softly.

The breath sighed out of him, shuddering and with an edge of tears. “You have?”

“Sir, you wanted me in that alley,” I insisted, and there was a bare hands-breadth between us. “Tell me, please. Do you want me still?”

“Yes,” he said. There was no hesitation in his voice. I have later learned that he, as I, believed he had simply crossed far too many lines that night to baulk at this small one.

I reached out to him, and I took his hand in mine and kissed it. “Will you have me, then?”

He surged against me, pressing close, reaching for my head so he could pull our lips close together. When he kissed me, I tasted the colour on his lips and the brandy from his tongue, and I willingly drowned in it. We grasped at each other, desperately kissing, until my fingers found the neckline of his dress. He shuddered under my hands. I drew back a little to look at him.

“Is this yours, sir? Shall we have to replace it if it is lost?”

“Call me Bertie, for God's sake,” Mr. Wooster said with a frown. “And, no, it's not mine. Just don't burn it tomorrow morning.”

I slid my hands down his sides, feeling the silk of the evening gown slipping under my touch. “Where did you get it?”

“They have this room in the club,” he admitted, gaze flickering. “You go and... and tog up, like this. Then you leave it all behind when you leave again.”

Cold fear trickled down my neck, dousing my desire. “Sir – did you leave behind anything by which you might be identified?”

He stopped, biting his lip, thinking. “I don't think so. Oh, God, Jeeves, what... what might I have left behind?”

“Your pocketbook, sir?”

“No, I didn't want to risk pickpockets, I only took the money with me,” he said slowly. “I've left behind a stack of dollars, but not enough to hurt.”

“Anything monogrammed, sir?” I insisted.

He shook his head. “No, just my regular evening wear. I know you didn't approve of those monogrammed pocket squares, Jeeves, so I didn't try to sneak them into my luggage.”

Then he blushed and looked away.

I smiled slightly. “I am grateful, sir, if only because you will not risk exposure.”

He looked up at me, then, wide-eyed, his red lip paint smudged and faded. My heart jolted in my chest. “Jeeves... Would you be angry if I told you I thought about you all night?”

I could not breathe. Mutely, I shook my head.

“I'm sorry,” he said, so softly I could barely hear him. “I never meant to... for this to happen. But the way you look at me when I wear something you approve of, well, it's just so... so bally marvellous! And I thought, if I looked enough like a filly, and a well-dressed one...”

He coloured again, then looked up at me. “I was just... dreaming.”

I reached a hand up to cup his cheek, rubbing gently at his rouged skin. “I do not enjoy women, sir. You are beautiful like this, but it is you I find thus, not the manner of dress.”

“You don't... you're like me, then?” he asked quietly, looking at me with astonishment. “Only coves for Jeeves, as Bertram prefers only coves?”

I nodded. “Yes, sir.”

He let out a deep, shuddering breath. “I've dreamed of you for ages, Jeeves.”

I leaned in slowly, to give him time to draw back, and kissed him gently when he did not. “That is another thing we share, sir.”

“And you're saying, I don't need the dress to have you look at me?”

“I would look at you if you wore rags, sir. You would be equally beautiful to me then.”

His eyes were loosing their hunted look, and his cheeks were no longer pale underneath his powder. He smiled at me. “So... call me Bertie?”

I could feel my face threatening to stiffen up. “I am not quite sure I can bring myself to do it.”

His smile widened. “The good, old feudal spirit too strong, eh, Jeeves?”

I forced myself to relax. “Reginald. My given name is Reginald.”

“Well, Reggie, will you come to bed with me?” Mr. Wooster said, looking shyly up at me.

I took a deep breath, through my nose, as slowly as I could manage. “Yes.”

Mr. Wooster grinned, then, looking younger than usual and very happy. “Oh, I say! Go through first, then, and I'll just get out of these things first.”

I did as he asked. I went into his bedroom, turned the bed down for him, and then hesitated. Ought I remove my own clothing? Were we progressing too fast, despite our lengthy acquaintance? Should we fall into this after the night we had just had? I removed my jacket and shoes, then waited.

“Well, here we are,” he said from behind me, and I turned to find him emerged from the bathroom, clad in a dressing gown and with his face glowing pink from vigorous scrubbing. He hesitated, rubbed at his ear, then took a step towards me.

“Are you... Reggie, are you sure about this? You're not just eager to get into bed with the young master after seeing him all made up like that, are you?” he asked.

“I swear to you... Bertie... I do not care about your garments. I have wanted you far longer than tonight,” I told him, and I felt myself blush a little, as he had done.

“Undress for me, Reggie,” he begged, and came to me to begin unbuttoning my waistcoat. “Let me see you.”

We removed my things, and at the sight of one of my braces still loosened from my trousers, Mr. Wooster's eyes went dark. He looked up at me, lips slightly parted.

“You were willing to be caught with me tonight.”

“Yes, sir – Bertie. But the probabilities were in our favour,” I said, hesitant to admit just how far I would have fallen for him.

“If they caught us, it'd be two years in Reading,” he insisted. His hands ran down my shirt and undid buttons deftly.

I breathed deeply. “Yes.”

“I know your brain is always in fine form, Reg, but tonight you really took the cake,” he muttered, grinning a little, and slid his hands around my middle inside my shirt. “Do you always think that quickly?”

I removed my shirt and he opened the buttons in my trousers. “I do not know, it is seldom required. But I should not hesitate to do so again. For you.”

He leaned up, and I took his mouth in a kiss. Our lips were still touching when his hands slid inside my underclothes, and I gasped against his mouth.

“I want you to continue what you were doing in the alley,” Mr. Wooster murmured into the skin of my neck as he lowered his face. “Only this time, I won't have bricks scraping against my back, and I want you to take off all the rest of your togs first.”

My breath caught in my throat. He was more open and less innocent than I had given him credit for. With haste, I removed the last of my clothing, and stood naked before him. He looked me up and down with an intensity and hunger I found beyond flattering. Then he quickly undid the belt on his dressing gown, let it fall to the floor, and turned to climb onto the bed.

“Come here, Reggie.”

I followed him, half hypnotised with lust, and went eagerly into his open arms where he lay on his back. When I sank down between his thighs, I could feel the silky smooth skin of his legs against my own, and this time, I allowed my groan to fill the heavy air between us.

“My God, Bertram, you feel...”

“You like it?” he asked, shy again. “I was... well, don't you know, for the costume, what?”

“Will you let me...”

And I moved down his body, kissing the skin that passed under my lips, until I was kneeling between his legs. I picked his right leg up and lifted it to my mouth, kissing his ankle. The skin slid like velvet beneath my mouth, and I pressed kisses all the way up his calf, his knee, his thigh. He moaned when my lips passed his hips and I released his leg to raise the other one.

“Reggie,” he moaned, “please!”

I kissed his other leg, rubbed my cheek against the softness of his inner thigh, but this time, when I reached his hip, I lowered my head to take him into my mouth.

“Reggie, God, yes,” he gasped, shifting restlessly underneath me. I sucked him with all the longing I had felt for two years and he arched up. “Reg, oh Lord, please, please...”

I took him deeper into my mouth, intending to bring him off in this way, but his hands buried into my hair and tugged impatiently.

“Up here, between my legs,” he insisted, when I raised my head to meet his eyes. “Just like we were in the alley, what?”

I complied, sliding up his body and gasping when our cockstands touched. He sighed happily and his hands came around my back once more. I leaned my weight on my elbows and thrust my hips against his, gently, and his eyes slid shut.

“Yes,” he encouraged me. “Yes, Reggie, I want you just like this.”

I panted against his neck, my breath hot on his skin, as I rolled my hips against his. His smooth legs came up around my hips and I stuttered, nearly losing control. He was divine in my arms; eager, open, warm and accepting. I kissed whatever skin I could reach and pressed us gently together over and over.

“Reggie, kiss me,” he pleaded, and I lifted my head, complied with all the energy I could muster.

“Oh, Lord, you're so lovely like this,” he muttered, pushing his hands into my hair again and smiling against my lips. “I've wanted you so.”

I could not speak; I was overcome with my need for him. I kissed him, begging him wordlessly to feel how I loved him, and rutted against him desperately. I was nearing my peak; I could not hold back when he was in my arms, pliant and golden, giving me everything I had silently wanted for years. When his hands slid onto my shoulders and he bucked underneath me, I could not stop myself. I came off with a groan, pressing close, feeling my desire slicking the skin between us as I rocked desperately through my climax.

“Oh, I say,” he breathed, and I shuddered. “Reggie.”

Still shuddering with pleasure, I raised myself off him, shifting a little to the side so that I might grasp him in my hand. He smiled at me and sighed happily as I began stroking him quickly, firmly, my own release slicking my grip.

“Yes, yes, Reggie, yes,” he panted, hips meeting my hand eagerly. I leaned in to kiss him, to swallow his sighs, and I felt his body tighten and tasted his moan as he came off in my hand. His body bowed bucked in my arms, his eyes were clenched shut, and I watched avidly as his release spurted from him, hot and wet on my hand.

“Oh, God, Reggie,” he gasped, shivering as he collected himself. “That was wonderful.”

I was still breathing heavily, looking down on him. His blue eyes were unfocused and dreamy. I kissed his reddened lips again, brushed his hair off his brow with my clean hand. He was more beautiful than anything I had ever dreamed, even in my dreams of him.

“I love you, old thing,” he told me, as easily as if he was talking of staying in for dinner. “I hope you know that. I don't go around shaking the sheets with just anyone, you know.”

I was speechless and could only stare at him.

He cocked his head to one side. “Do you not love me? I'm rather certain I heard you admit something to that effect earlier, in a roundabout way. You've not changed your mind?”

I gathered what remained of my wits. “I do love you. I am only a little... surprised.”

“Well, yes, I suppose I have been full of surprises tonight,” Mr. Wooster agreed with a smile. “The dress, for one. And shaving my pins like this. Oh, and nearly getting caught in a nightclub raid, although you've had to bail me out before, so perhaps that was less surprising.”

I cupped his cheek and held his face so I could lean our foreheads together. “What is surprising is your reciprocation of my feelings.”

He scoffed, but allowed me to gently rub my face against his. “Tosh, Reggie. Of course I love you; how could a man in his right mind be an invert and not love you? That's just silly. Are you sure you weren't shocked by my costume tonight? Your sartorial sensibilities deeply offended?”

“You were very well dressed, sir. There was nothing at which to take offense.”

“Don't call me sir in bed, Good Lord.”

“Bertram.”

“Oh, I say, it gives me all sorts of ideas to hear you say my name in that way. Indecent ones, you understand.”

I kissed him again. “I shall be agog to hear your ideas, Bertram. I am certain we shall be able to do something with them.”

He laughed with delight underneath me. “With your fish-fed brain and my shocking imagination, Reg, we shall be the absolute top. The toast of the Drones club, although I shall have to censor my stories somewhat.”

I smiled into the skin of his chest and pressed a kiss just over his heart. “I believe we shall.”