All In: A Poker Night Submission

Tonight's poker night at Leo's, and I can feel the tension building. He's been talking it up for weeks, and it's not just about the cards or the money--it's about putting me on display. His perfect little sissy, humiliated in front of his buddies.

But right now, I'm still David, doing the errands like a good boy. Jenny hasn't fully taken over yet, though she's itching to break free. Today's about one thing--being Leo's little slut. I've got on these stupidly tight baby blue shorts that barely cover my ass. They're squeezing me so hard I can't even breathe. On top, Leo's got me in this baby pink tank that's practically screaming, "I'm a little bitch." No hiding in this getup.

And to top it off? Pink fucking sunglasses. Big, round, and ridiculous. I look like a joke, and that's exactly how Leo wants it.

But what really gets me is this fucking cock cage. Locked tight. No touching, no feeling, nothing. Just a constant reminder that I'm his, and nobody else is even allowed to look. It's thrilling. And it fucking sucks.

Leo's sitting there, watching me, a smirk plastered across His face. "You look like a fucking idiot, boi," He says, enjoying every second of my embarrassment. I feel my face heat up, but I don't dare talk back. That's not what today's about. Today's about humiliation.

"You're gonna run your errands just like this," Leo commands, crossing his arms. That devilish look in His eyes tells me He's enjoying this a bit too much. "And don't forget what you are. I want everyone to see my little sissy boi. No hiding."

I swallow hard, nodding. What the hell's the point in arguing?

"The guys will be here at 4," He says, like it's just any other day. "You get everything we need, and be back in time to get dolled up. You're the fucking star tonight, babe. This isn't just about poker."

My stomach twists. The main attraction. First, I've gotta parade around like this, then turn into Jenny for poker night.

"You'll set everything up, and then present yourself as a good little whore," he adds, smirking wider. "Everyone needs to know what you're good for."

I nod, trying not to lose it. Leo's friends are gonna see me like this, knowing I'm his locked-up little slut. Humiliating as fuck. And yeah... it turns me on sooo much.

So, I get into my car and drive to the supermarket.

Now I'm pushing a cart through the grocery aisle, trying not to make eye contact with anyone. These damn pink sunglasses feel like a neon sign screaming, "Look at this freak!"

The shorts are cutting into me, and the lock's pressing right against the fabric. I'm praying no one notices, but, of course, life's gotta fuck with me.

This old guy--seriously, could be my grandpa--walks by, and I can feel his eyes on me before he even opens his mouth. "Well, don't you look pretty today," he says, grinning like he's in on the whole fucking joke. My face is burning up. It's like he can see right through me, see all the twisted shit Leo's got me doing.

So, I'm just trying to get through the damn store when this old guy walks past me, kinda grinning like he knows something I don't. "Well, don't you look pretty today," he says, and immediately my stomach drops. It's that condescending, "I'm-gonna-judge-you" tone that makes me feel like a damn freakshow. My face is on fire, but I try to ignore it and just keep walking.

But of course, I can feel his eyes on me the whole time. I try to focus, but it's like I can't shake the feeling that he's looking me over, like I'm some kind of experiment. I can feel him drinking me up--like, straight up checking me out--and that's when I turn around. And yeah, he's still looking, but not in the way I thought. He's practically undressing me with his eyes, like I'm his personal little show.

That's when it clicks. I know exactly what Leo would say: "You're gonna make him want you. That's your job, baby." And fuck, I'm trained for this. So, I give him a little look, a smirk, and start walking a bit slower, just letting my hips sway. I know he's watching, and I love it. I do my best to give him that perfect little sissy walk, like I'm here to put on a show.

And I can tell he's into it--hell, I can practically hear him drooling.

Alright, focus, Jenny. You've got this. Bulleit's locked down. Now for the rest of the shit. Leo didn't give me a list, of course. I'm just supposed to know what he needs. Classic.

I start grabbing stuff off the shelves like I'm on some shopping spree. Chips? Yeah, I'm grabbing three bags, not one. Nuts? Make it five different kinds. I'm tossing in all the snacks I can find--popcorn, pretzels, some weird spicy thing I've never seen before. Leo's buddies like to snack while they play, so fuck it, I'm overbuying. I want to make sure there's enough, even if the game goes on until morning.

I hit the mixers next--ginger beer, club soda, cola--basically, I'm loading up on everything. I don't care if it's excessive. I'm not about to hear Leo complain that I didn't get enough. I throw in more than enough ice to keep everything cold, even though I don't know if they'll drink it all.

Then, beers. Oh, fuck yeah. I grab six packs--no, make that eight. If anyone needs more beer, I'll have it covered. It's about making sure they've got everything they want, and I can't risk coming back with anything missing. It's like if I don't overdo it, I'll be setting myself up to fail.

I roll my cart down the aisle, checking things off in my head. Snacks? Covered. Drinks? Covered. Ice? Check. But I can't leave without adding something a little extra.

I grab a couple packs of cigarettes. Who knows? Maybe someone will want one. It's one of those things that feels like I should have it, even if it's just to say I'm prepared.

And then it hits me. I want to make something myself. Something more personal. I'm sick of just throwing things in bowls like some lazy fucking idiot. I want to do better, show Leo that I can add a little flair, make it feel... well, a little more feminine. I head to the deli counter and pick up some prosciutto, a couple fancy cheeses, a bit of pâté. I figure I'll put together a nice little charcuterie board--real European style. It'll probably get ignored, but fuck it. If I'm gonna be the good little slut tonight, I'm gonna do more than just keep my mouth shut and pass out the snacks.

They'll probably just grab the pretzels and leave the fancy shit untouched, but whatever. At least Leo'll see I'm not just a robot who buys shit and puts it in bowls. This is my little way of showing him I'm more than just a sex toy in tight shorts. (or am I?)

I feel the weight of the bags in my hands, the small pride of doing something right, but that pride quickly fades. Time's running out. I'm eating into my getting-ready time, and there's still so much to do. I can't be late for Leo, and everything has to be perfect. Not just my look, but the whole damn night. I need to turn into that perfect version of Jenny He'll want to show off, have everything set up, and make sure He's got His favorite drinks and snacks waiting. It's all for Him, and I can't screw it up. And on top of the tight timing, I decided to make a fancy board. Fuck. I hope I can pull it off.

I make it home without getting pulled over for speeding--thank God, because I'm in such a rush. First thing's first: shower. Gotta be smooth for Daddy. No excuses.

I take my time shaving every inch--legs, arms, everything. Leo's got standards, and I'm not about to disappoint. Then comes the moisturizer. Slather it on thick. Smooth skin's a must, especially with the latex He picked out.

After the shower, I slide the chest plate on. DDs, baby. These things are huge, heavy, and fucking perfect. I adjust it, making sure it sits flush against my skin, and let out a little sigh. Feels like I'm one step closer to becoming the version of me that Leo wants.

Now, makeup. No holding back tonight--heavy contouring to carve out these cheekbones like they're sculpted from stone, eyeliner so thick it's borderline sinful, and lashes long enough they almost touch my eyebrows. A thick swipe of gloss to finish it off just enough to look like a working girl.

Once I'm satisfied with my face, I check myself out in the mirror. Shit. I look insane. Huge-busted, tiny-waisted, ready to have Leo lose his mind. I've never been this thin in my life, and Leo's workout routine is paying off. My waist is tiny, my hips pop like crazy, and I can already see the look on Leo's face when He sees me like this.

Now for the clothes. The corset goes on first, pulling everything in tighter, making my waist even smaller. I know I'm gonna feel it all night, but I'm already starting to get excited about how ridiculous I'll look in this outfit.

.

Next up, nails--bright pink, long as hell, and totally impractical, grabbing anything with these claws is like forget it. I'm practically relearning how to use my hands, but I take my time and get them perfect because at the end of the day, it's all about the look. Although time is something I don't have a lot of, gotta keep going, Shit, I lose myself so easily doing this kind of thing.

Now for the latex. I slide into this black latex miniskirt, and holy shit, it's short--way shorter than anything I've ever worn. And I usually dress like a slut. Every step flashes a bit of the garter belt, thick metal buckles holding up black fishnets. The fishnets cling just right, giving a peek without giving it all of my lace thong away.

Time for the accessories--long-ass earrings that brush my shoulders, swinging like they're trying to catch someone's attention. And they will. Then the wig--long, straight, jet black. I throw it on, and it falls like silk down my back. A couple of brush strokes, and it's sleek and glossy, like I just stepped out of a high-end salon.

I grab my phone and text Leo: "I'm here, Daddy. About to get everything perfect for you. Outfit's on point. Can't wait for you to see your slut."

He replies fast: "Good girl. Make sure those tits are popping, slut. Guys are gonna love the view. Don't fuck up the setup, or you won't sit for a week."

My heart skips a beat, and I feel my legs go weak. But this is what I'm here for. Time to get to work.

Heels will have to wait if I want to do this fast. I have so much to do and so little time. But I know He'd rather have me perfect than the party setting, although he is expecting both. I know,

First stop: the kitchen to set up the booze. Leo's bougie bourbon front and center, a couple bottles of top-shelf whiskey for the guys, and some beers for the basic bitches. I smirk a little, thinking how Leo's so damn particular about this stuff. But that's just who he is.

Next, snacks. I set up a few bowls--chips, nuts, dip. Nothing that needs cooking. I'm not about that tonight. Then, the poker table. Cards stacked, chips neat, and a spot ready for His cigar. It's all about the details with Him.

Before I put on the heels, I need to prep the board. Fuck, why did I decide to go all out with this? It's just one more thing eating into my time. But I can't skip it; Leo loves the little details, and the board will give everything that perfect, classy touch. I lay out the prosciutto, cheeses, and pâté, arranging it like I'm making some kind of fancy spread. I even made flowers out of the prosciutto--stayed up late last night watching videos like a good housekeeper, making sure I got it just right. Yeah, no one will care, but it'll look good, and that's what matters.

Next, the heels--six inches, with only an inch platform. Every step is a test to stay upright, and I'm balancing on my toes, feeling the burn already.

I slide on the heels--six inches, with only a tiny platform, so I'm practically balancing on my toes. The minute I stand, I feel the burn shoot up my calves, but I push through it. Leaning against the vanity for a second, I catch my reflection, and damn, I look fucking hot. But these heels... I'm not sure I'll last the whole night in them. I let out a breath, thinking, How the hell am I gonna get through this night in these?

I grab my phone, snap a quick pic, and send it to Leo. "All set, Daddy. Place is ready, and I look like your slut. Can't wait for you to see."

Seconds later, he's back. "Good girl. Get ready to be shown off, bitch. You'll keep those heels on all night."

I suck in a breath. Tonight's gonna be brutal.

Then, the doorbell rings, and my heart does a damn flip. I open the door, and there's Leo, grinning like he's got the whole night figured out--and let's be real, he probably does. His eyes sweep over me, taking in the whole look, checking if everything's exactly how he wants it.

"Well," he smirks, "you gonna invite us in, or what?" He says it like I'm just standing there for decoration. I step aside without a word, trying to keep it together.

The first guy walks in--Jake or some shit--and just stares at me like it's no big deal. Doesn't say a word, just throws his jacket into my arms. "Put that somewhere, yeah?" Like I'm a damn coat rack. I don't even flinch, just take it and move.

Next is Mike, swaggering in with a six-pack in hand. He hands it over, but not before his hand "accidentally" brushes my chest. "Here, sweetheart, don't spill it." Yeah, because balancing this crap in heels is so easy, right? He smirks like it's all one big joke. I force a smile and hold it together. Can't let Leo down.

Then the last guy--Tony or something--comes in already grinning like a creep. He pulls me in for a hug, his hand going straight to my ass, squeezing like he owns it. Breath hot on my neck, he whispers, "Leo wasn't kidding. You're a real fucking tease, huh?"

I'm standing there, arms full of jackets and beers, ass out for all to see. Fantastic. He laughs, slaps my ass hard making me jum, I almost drop everything I have in my hands, and saunters off like nothing happened.

Leo's just standing there, watching with that smug grin. "Good girl," he says. "Now, get 'em settled. Make sure they've got everything they need. You know the drill."

And there I am thinking, yep, just another fucking day.

"Oh and, Baby" he says. "You look perfect, good job". That just makes my day, anything else that happens now is worth it.

So, after shoving the beers in the fridge and catching my breath, I head back to the dining room. The guys are already kicked back, lounging around the table like they own the place. I know Leo's watching, so I stand like he taught me--ankles together, hands crossed, shoulders back, chin up. Perfect little servant on display.

My heart's pounding, but I pull out that high-pitched, fake-sweet voice Leo loves, trying to sound all soft and feminine. "Good evening, gentlemen," I say, feeling the words Leo drilled into me roll out like a script. "I'm here to serve you tonight. Whatever you need, just ask."

It feels ridiculous, but one look at Leo's face keeps me in line. Paul raises his eyebrows and smirks. "Well, aren't you polite? Could've fooled me with that outfit," his eyes dragging over me again. I swallow hard and keep that fake-ass smile plastered on.

"Get me a beer, babe," Mike says, like I'm some waitress at a shitty bar. Doesn't even look at me, too busy shuffling cards.

"And I'll take a whiskey, doll. Make it neat," Paul chimes in, checking me out again. "And hurry up," he grins, like he's daring me to snap back.

I nod, turn to leave, but I hear one of them--doesn't matter which--grumble, 'She's one slip away from breaking her fucking neck in those heels, man. I bet Leo's got a backup model just in case.' The whole table cracks up, Mike slapping the table so hard the cards bounce.

"Leo, man, you really know how to pick 'em," Mike cackles, "Look at that ass! Tight."

My hands are shaking as I head to the kitchen, but I keep that stupid smile on my face, even though I'm ready to scream inside. It's like I'm a toy for them to gawk at, a joke. And Leo doesn't even flinch, just leans back in his chair, watching like he's proud of his little creation.

In the kitchen, I'm mixing their drinks, but there's this weird thrill bubbling up inside. This is so fucked up... but hot as fuck. I grab the whiskey, pop open a beer, and throw in a bowl of pretzels and chips like I'm being some Playboy Bunny type. But this shit is way harder than it looks--especially in these heels and this tight-ass skirt. My boobs are about to spill out, and every time I bend down, I feel like I'm gonna face-plant.

Balancing everything on a tray, I wobble my way back into the room. The second I step in, they're all staring at me like I'm some prize. Comments start flying again, same bullshit.

Mike whistles, leaning back. "Look at that little sissy go, damn. Those heels giving you trouble, sweetheart?"

I try to do the whole 'bunny' act, serving drinks with a smile like I'm not about to eat shit.

Every time one of them looks at me, it's like their eyes are burning holes in my skin. I set the whiskey in front of Paul, lean over with the beer for Mike, and try not to trip.

"Careful there, princess, wouldn't want you to break a nail," Mike laughs, his hand brushing my thigh as I set down the pretzels. My heart's racing. They're messing with me, testing to see how far I'll go, and Leo's just sitting there, grinning. Like I know it's all part of his plan.

Once everything's served, I stand up straight, ankles together, hands behind my back.

"Anything else, sirs?" I ask, trying to keep my voice steady, knowing I'm more of a joke to them than a server.

They don't even bother answering. Just keep talking, barely glancing my way. Then Paul nudges Leo, smirking. "So, she any good at sucking dick, or what? Looks like it's in her fucking DNA to do it right."

Leo just grins, his hand casually sliding over the back of my leg. "Maybe you'll get to see by yourself later, we'll see how it all goes"

They all laugh, tossing even more crude comments around like they're at some frat party, which they all are. I always despised frat boys and here I am serving them today.

"Bet she takes it all, huh? Look at that mouth--probably made for it, huh? That lipstick ain't just for decoration, is it?" The table erupts into laughter, and I stand there, stiff as a board, trying not to let my nerves show. But my heart's pounding in my chest.

Every look, every comment--it's humiliating as fuck, but it's hot. I feel like I'm melting under their words, trying to keep it together while they tear me apart.

Paul smirks at Leo, "Seriously, Leo, how much did you pay for this little piece of ass?"

"Don't think it's a piece, bro," Mike says, sipping his beer. "More like a whole damn set. She's got everything we need."

"Bet she's a real handful," Sam adds, his eyes roaming all over me. "What do you think, Leo? Bet she's a needy little thing, huh?"

"Yeah, she's a handful, alright," Leo chuckles, clearly enjoying this. "But she's built for it. Better than the real girls, man. Gurls like her? They take it all. They were born for it."

I feel the heat rise in my cheeks, but I keep my chin up, sticking to the act. "I'll be serving you all night, so just ask for whatever you want!" I squeak, my voice high-pitched like Leo taught me.

Paul smirks, his eyes gleaming with that smug shit. "Water chasers for all of us, and one for you, honey. Wouldn't want the little slut passing out on us while she's working, right?"

I force a smile, voice cracking a little, "Sure thing!" I grab the tray, trying not to stumble as I head back to the kitchen, their cruel words echoing in my head.

As I'm walking away, Mike calls out, "Leo, you think she'd make some extra cash on the side? I'd throw down to see that!"

"Shit, she's got that look about her," Paul chimes in, leaning back with a grin. "She'd be raking it in, no doubt."

Sam snickers, eyes scanning me like I'm his personal joke. "Yeah, she looks like she got picked up off the street. Not charging by the hour, are you, sweetie? Shouldn't be too expensive for what she's offering."