Leah and Gregory — AI by author

Leah and the (Much) Older Man — Part Fourteen

After a week of being Leah, Gregory asks her to switch to Baby for the evening…

[embed]List: Leah and the (much) older man | Curated by P.T. Brown | Medium Leah and the (much) older man · Eighteen-year-old Leah meets a handsome older stranger on a park bench, and her sex…medium.com

The week has been a slow, delicious kind of torture.

I’ve been at Gregory’s house every single day. Mornings, afternoons, sometimes until late. My parents think I’m out with Emily, or shopping, or “just hanging around town.” They have no idea I’m spending my days naked in a sixty-year-old man’s mansion, letting him fuck me in every room.

We haven’t played Baby and Papa once since we got back from the castle. No pink cuffs, no pigtails, no being told what to call him. I’ve just been Leah. Adult Leah. The girl in a little sundress or silk slip who wanders into his study while he’s on a call and drops to her knees under the desk. The one who bends over the kitchen island while he’s making coffee and pushes her knickers down. The one who rides him on the sofa in the middle of the afternoon with the curtains wide open, moaning his name like I don’t care who hears.

And I don’t. Not here. This house is our sexy space. It’s just a shame I can only stay overnight occasionally — don’t want to make mum and dad suspicious that their innocent little eighteen-year-old is now far from as innocent as they think she is. But this weekend, Saturday, I’m staying.

Underneath all the sexy fun we’ve had this week, I’ve been aching. Aching to be Baby again. Aching for the clothes, the rules, the way he looks at me when I’m small and sweet and filthy all at once. Every time he’s come inside me this week, I’ve wanted to whimper “Papa” instead of “Gregory.” Every time he’s spanked me or pulled my hair, I’ve wanted to slip into that high, breathy voice and beg. But he hasn’t asked. And I haven’t pushed. I’ve just stayed Leah, which still results in him screwing my brains out at least twice a day.

Friday afternoon, when I’m leaving to head home, he walks me to the door. I’m in black jeans and a little top, hair loose, looking like any normal eighteen-year-old girl heading home, except I have two loads of a sixty-year-old man’s come leaking into my underwear and the crotch of my jeans. He kisses me slowly and deeply, one hand on the small of my back, and then he pulls back just enough to look me in the eye.

“You’re going to be Baby tomorrow night.”

The words hit me low and hot. My stomach flips. My pussy clenches around nothing but the mess that he left inside me, forcing more out. I swallow. “Fuck, yes, please. And before then?”

Gregory smiles that slow, knowing smile that always makes my knees weak. “Come early. Spend the day here. Pamper yourself. Get ready. Oh, and try on all the new outfits that are arriving for Baby first thing in the morning. You can pick one for tomorrow night.”

There’s a glint in his eye. Something deliberate. Something planned. I feel it bloom between my legs again, hotter this time.

“Yes, Papa,” I whisper, even though I’m still dressed as me. He kisses me once more, soft and possessive. Then he rubs his fingers against the damp patch in my jeans and sends me home.

I’m back before nine on Saturday morning, practically vibrating.

Gregory’s sitting at the kitchen island, sipping coffee in his dressing gown. He looks up when I let myself in with the key he gave me last week, and his smile is warm but edged with something darker.

“Morning, sweetheart.”

“Morning.” I drop my bag, kiss him hard, and then glance around. “Where’s the delivery?”

He nods toward the garden. “In your playhouse.”

The word makes me smile. He’s never called it that before. It’s always been the summer house. Now it’s mine. My playhouse. Baby’s den of sin.

I kiss him again, quick and hard, already moving. “I’ll be back.”

“Take your time,” he calls after me. “Pick one you like. Surprise me with it later.”

I run to the summer house. Inside, in the middle of my childish bed covered in teddy bears just for effect, sits a large white box tied with a pink ribbon. I tear into it like a kid at Christmas. And oh my God.

The clothes inside are even younger, even prettier, even more obscene than anything he’s put me in before. They aren’t young with an edge. They are perfect innocence. Tiny frilly dresses in pastel colours. Various socks with little bows. Another pair of shiny black Mary Janes after I lost the last pair at the baby getaway. A headband with a big satin bow. And tucked underneath, the accessories: an adult-sized dummy with a pink ribbon, a soft pink rattle shaped exactly like a little cock, complete with veins and a flared head. There’s even a small pink bottle with a teat.

I bite my lip so hard it hurts.

I sort through everything slowly, running my hands over the fabric, imagining how each piece will look on me. How it will feel. How Papa will look at me in it. What he’ll do to me in it.

I settle on the one that makes my stomach flip the hardest. Tight white frilly knickers, the kind that sit high on the hips and hug everything. And over them, a red-and-white checked dress with a high Peter Pan collar, short puffed sleeves, and a hem that falls all the way to my knees. It’s the most innocent thing I’ve ever seen. The kind of dress a sweet girl would wear to church or a birthday party. On me, with nothing underneath but those obscene little knickers, it’s going to look positively filthy.

I fold everything else carefully and put it away in the wardrobe. The dummy, bottle, and cock-rattle go in the drawer beside the bed. I leave the dress and knickers on the bed for later. Then I head back to the house.

Gregory’s still at the breakfast table. He looks up when I come in, eyes flicking over my body. I stop in the doorway and lick my lips slowly, deliberately.

“I’m going to look scandalously young and innocent later.”

His mouth curves. He sets his coffee down, reaches out, and pulls me straight into his lap. I go willingly, straddling one of his thighs, my arms looping around his neck.

“Good girl,” he murmurs, gently teasing a nipple through my top with his fingertips. His hand slides down between my legs, cupping me through the denim. Even through the thick fabric, I know he can feel how hot I am. I sigh and part my thighs for him without thinking, wanting more. He presses the heel of his hand against me once, firm and teasing, then pulls away.

I whimper. The sound slips out before I can stop it.

“No,” he says quietly. “I want you completely desperate later.”

“I’m already completely desperate,” I protest, shifting on his thigh. “I’m always desperate around you.”

Gregory’s eyes darken with approval. “Then I want you even more desperate.”

I pout. Full bottom lip, big eyes, the whole thing. He laughs, low and warm, and gives my ass a little squeeze.

“Go upstairs and pamper yourself. You can dress in the playhouse later.”

I stand up slowly, making sure he watches every movement. Then I peel my vest off over my head, drop it on the floor. Unbutton my jeans and push them down, stepping out of them. No bra. No knickers. Just me, naked in his kitchen in the morning light. I let him drink me in, hoping he’ll jump me, but he doesn’t. Bastard.

I gather my clothes in one hand, turn, and start walking toward the stairs, hips swaying. “If you change your mind…” I call over my shoulder, voice sweet and teasing.

“I won’t,” he replies, amused.

I pout again, even though he can’t see it, and keep walking. I’m halfway up the stairs when his voice follows me. “And no playing with yourself in the bath.”

I stop. Turn my head just enough to answer in that high, childish register I know he loves.

“Yes, Papa.”

The word hangs in the air between us. I hear him chuckle softly downstairs.

Gregory leaves just after lunch, kissing the top of my head as I’m relaxing in the bath and telling me he’s popping into town for a few things. I finish my bath in the enormous marble tub in the master en-suite, taking my time with the razor, gliding it carefully over every inch of skin until I’m silky smooth. Then I slather myself in the expensive lotion he keeps for me, rubbing it in slowly, deliberately, my hands lingering on my breasts, my stomach, the soft skin of my inner thighs. I’m already swollen and sensitive. Every touch makes me sigh. By the time I’m done I’m aching.

I pad naked across the bedroom and climb onto his big bed, rolling onto my stomach with the new book he bought me last week. It’s filthy. The story of a girl called Amy who starts having secret outdoor sex with her university professor — a man easily old enough to be her father — and ends up becoming an elite escort. The sex scenes are intense. Detailed. Unapologetic. I read with my chin propped on my hands, legs kicking lazily behind me. Every time Amy willingly wanders into that dark alleyway to meet the professor to be subjected to something filthy, my pussy clenches, and I have to press my thighs together.

It doesn’t help, though. It makes everything worse.

I roll onto my back, one hand drifting down my stomach without thinking, but I stop myself. Papa said no playing with myself. I groan out loud and drop the book on my chest, staring at the ceiling, nipples tight, pussy slick and empty and throbbing.

By the time I hear the front door open downstairs, I’m half out of my mind. I slip into one of the tiny silk robes he bought me — pale pink, short enough that it doesn’t even cover the curve of my ass, the fabric so thin it clings to my damp skin. I tie it loosely and wander downstairs barefoot.

Gregory’s in the kitchen unpacking a few bags. He looks up when I appear in the doorway, and his eyes darken instantly. He crosses the room in three strides, pulls me straight into his arms, and kisses me hard — deep and possessive, one big hand sliding down to grip my bare ass under the robe. I melt against him, moaning into his mouth, already trying to press closer. It’s clear that he’s struggling with this temporary sexual restraint as much as I am. Then he pulls back.

Just like that.

He turns away to put something in the fridge, and I’m left standing there, lips swollen, robe half open, pussy pulsing.

“Papa better fuck Baby into next week tonight,” I grumble, voice low and sulky. Gregory glances over his shoulder and smiles. That calm, knowing smile that always makes me want to stamp my foot at him and gag on his cock.

“We’re having an early dinner,” he says. “Then I want you to go and get ready.”

My stomach flips. “I’ll do my hair and makeup in the playhouse,” I say sweetly. “Then I’ll dress and come back up.”

“No.” His voice is quiet but firm. “You’ll wait there for me.”

Heat blooms low in my belly so fast it makes me dizzy. If he’s coming down to the playhouse himself… that means he plans to tie me up. Really tie me up. The kind of sex where I’m not going anywhere until he’s finished with me. I swallow. My voice comes out smaller than I expect. “Okay.”

In the playhouse, I take my time with my look. Tonight needs to be perfect. Not like the baby getaway when I just wore something young-looking and fucked other men under his watchful eye. I have a new outfit, the least I can do is look…

I draw little freckles across the bridge of my nose with my special pencil. I do subtle makeup, soft and sweet — big eyes, soft, glossy lips. The headband with the big satin bow goes on last, sitting perfectly in my hair.

I step into the tight white frilly knickers, then the red-and-white checked dress. It falls to my knees. The Mary Janes and the little white ankle socks with pink bows on them complete it. I look at myself in the full-length mirror and feel my stomach flip. I look scandalously young. Scandalously innocent. And I know exactly what that does to him.

I pick up the little cock-shaped rattle in one hand and the adult dummy in the other, turning them slowly. I can feel how wet the frilly knickers are getting already.

Through the window, I see Papa coming down the garden path, right on time.

I slip the dummy between my lips, sit down on the edge of the bed, and clasp my hands in my lap like a good girl. The rattle rests beside me. I keep my knees together, ankles crossed, and look up at the door with the sweetest expression I can manage.

Gregory stops dead in the doorway. “Fuck,” he mutters under his breath.

I suck gently on the dummy, letting it move between my lips. His eyes go dark instantly. He steps inside and closes the door behind him, never looking away from me. When he reaches for the dummy, I suck harder, giving him a little resistance, just enough to make him work for it. He pulls it free with a soft pop, and a string of spit connects my lips to the teat for a second before it breaks.

I tilt my head, flutter my eyelashes, and let my voice go high and soft and childish.

“Hi, Papa.”

Gregory’s throat works as he swallows. He takes my hand and pulls me gently to my feet. The dress swishes around my legs. “Hi, baby,” he says, voice low and rough.

I look up at him with big eyes. “What do you want to play tonight, Papa?”

He smiles, slow and dark. “Pass the baby.”

I blink, genuinely curious. “What?”

“There are some daddies at the house who want to play with you.”

A full-body shudder runs through me. Heat floods between my legs so fast I have to press my thighs together. “How many?” I whisper.

“Enough to keep Baby busy for a while.”

I glance past him, out the window toward the big house, and feel my pulse kick hard. My nipples are tight against the inside of the dress. My knickers are soaked.

“What should I do with them, Papa?” I ask softly.

Gregory cups my chin, thumb brushing my bottom lip where the dummy had been.

“Do anything they tell you to do.”

I smile, sweet and obedient and already trembling with excitement.

“Yes, Papa. Take me to meet them.”

Gregory takes my hand and leads me up to the house in silence.

I’m so excited I could burst. My heart is hammering, and every step in my little Mary Janes makes the frilly dress sway around my smooth legs. I don’t speak. I just let him guide me, eyes down, letting the anticipation coil tighter and tighter inside me. He takes me straight to the library.

It’s a vast, warm room with deep leather chairs arranged all around the sides and the big snooker table in the centre. Gregory leads me through the door by the hand, my eyes still on the floor, then stops me near the snooker table. He steps behind me and rests both hands firmly on my hips.

“Gentlemen,” he says, calm and proud. “This is my baby girl.”

I lift my eyes and scan the room.

Eight smiling older faces look back at me. All of them are Papa’s age or older. Well dressed. Handsome. They look at me like a pack of wolves would look at prey.

Perfect, I think. “Hi, Daddies,” I squeak.

It’s only then that I really notice the snooker table. I’ve been fucked on the edge of it, and bent over it enough times to know it’s never covered. But today it is. It has been covered with a large black rubber sheet that drapes off all sides and onto the floor. There’s a large bottle of body oil, a bottle of lube, and a small white pillow placed right in the middle.

It lands deep within me. I know immediately that I’m not leaving this room without fucking all of these men at least once. The smile that crosses my face is so wide it almost hurts.

Gregory’s hands stay on my hips for a moment longer. Then he leans down and speaks softly against my ear.

“Go and greet everyone properly, baby.”

I nod, already flushed with excitement, and begin to move slowly around the room.

I go to each man in turn, leaning down with my hands clasped sweetly in front of me, parting my lips for each of them to taste my mouth. The first one kisses me gently, his hand resting warm on my thigh just above the knee. The next one slides his palm up the back of my leg as I bend towards him, fingers brushing the edge of my frilly knickers. Another cups my ass through the dress and gives it a slow, appreciative squeeze. When I reach the fourth man he kisses me deeper, one hand sliding up to cup my small breast through the checked fabric, thumb brushing over my nipple before giving it a gentle squeeze that makes me whimper into his mouth.

By the time I’ve made my way around all eight of them and returned to Papa, my cheeks are hot and my lips puffy from kissing eight men.

Papa turns me to face the room again and reaches for the zip at the back of my dress. Slowly, deliberately, he peels it down my body until it pools at my feet. I’m left standing in nothing but the tight white frilly knickers, the little white socks, the Mary Janes, and the headband with its big bow.

“Climb onto the table, baby,” Papa says quietly. “Oil your body for them.”

I climb up eagerly, the rubber sheet cool and smooth under my touch. I lie back in the centre, spreading my legs wide so the tight knickers pull taut and flash the damp crotch to the men watching from the shadows. I pour oil into my palms and begin to rub it slowly over my breasts, circling my nipples until they’re shiny and stiff, then down over my stomach and along my thighs. The men are silent, but I can feel every eye on me.

“All of you,” Papa commands from somewhere in the darkness.

I smile around the thought of it and put on a proper show. I hook my thumbs into the waistband of the frilly knickers and peel them down my legs, dropping them off the side of the table. Then I part my knees wide, pour more oil directly between my thighs, and massage it slowly into my pussy and ass, letting my fingers slide over my swollen clit and between my cheeks. Oil pools on the rubber sheet around my naked body, making everything slick and shiny under the bright table light.

Gregory’s hand reaches into the circle of light. He presses the dummy between my lips. I suck on it obediently and taste the expensive whisky he lets me have when I want to get really naughty. I smile around the taste on the teat, eyes half-lidded, and lie back again, letting them all look at me — naked, oiled, legs spread, only the Mary Janes, little white socks, headband and dummy left to remind anyone I’m still playing at being young.

“Gentlemen,” Gregory says, voice calm and clear. “She’s all yours. And she’s such a good girl, she’ll do pretty much anything you tell her. Won’t you, baby?”

I blink up toward the darkness where I know he’s standing, the dummy still in my mouth, and nod slowly, the teat jiggling as I suck on it.

I can hear movement now. Belts unbuckling. Clothes being removed. The soft sounds of eight older men getting ready to use me.

I’m so excited it could be Christmas morning.

I lie there in the centre of the brightly lit snooker table, completely naked, skin shining with oil, the little pink ribbon on the dummy resting on my chest. The first man steps forward. He is completely naked — broad shoulders, a thick cock already hard and curving upward. He climbs onto the table from the side, the rubber sheet shifting under his weight as he moves toward me on his knees. He doesn’t say anything at first. He just takes the dummy from my lips and then straddles my upper body.

“Open,” he says quietly.

I open my mouth, and he grips my head and pushes his cock straight into my throat. I gag hard, eyes watering, but I don’t try to pull away. He holds my head with both hands and starts fucking my face in slow, deep strokes.

Another man climbs onto the table from the other side. He is leaner, with salt-and-pepper hair on his chest. He kneels between my spread legs and runs his hands slowly up my oily thighs before pushing two fingers into me. I moan around the cock in my throat.

“Fuck, Gregory, she’s perfect,” the man fucking my face mutters.

“Such a pretty little pussy,” the one between my legs says, almost conversationally. He curls his fingers and I jerk, my hips sliding on the rubber. They take their time with me like that for a while — one using my mouth, the other fingering me — until the first man pulls out of my throat with a wet sound and comes across my breasts in thick ropes. He rubs it into my skin with the head of his cock before climbing off. The second man immediately takes his place.

He too climbs high up my body, straddling my chest, but he pushes his cock between my small, slippery breasts. He squeezes them together and starts fucking them, the head of his cock bumping against my chin with every thrust. I open my mouth and lick at it whenever I can reach.

“Such pretty little tits,” he grunts.

A third man appears between my legs and slides his thick cock into me, fucking me in long, steady strokes. Every time he thrusts into me, my whole body slides a few inches up the table. The man using my tits has to keep adjusting his grip on my shoulders to keep me in place.

I am already a mess — oil and come smeared across my chest, spit running down my chin — when Gregory’s voice comes from just outside the circle of light.

“That’s it, baby. Good girl,” he soothes.

I whimper happily around the cock bumping against my lips.

The men start rotating. When the guy between my breasts comes all over my chin and face, he climbs off, as does the guy who was fucking me, without finishing. No doubt he will later. Another man climbs onto the table and turns me onto my hands and knees. The rubber sheet is so slippery now that I keep sliding. He has to grip my hips hard to keep me steady as he pushes into my pussy from behind. I cry out happily. I think I have been doing that a lot. Another man kneels in front of me and feeds his cock into my mouth, and my cries are muffled.

I am relentlessly fucked from both ends, sliding back and forth between them on the oily surface. Eventually, the man behind me pulls out and slides a finger into my rear, testing. I pull off the cock in my mouth just long enough to speak, my voice high and sweet.

“You don’t need the lube, Daddy,” I say, looking back at him over my shoulder. “I’m so oily… it’ll go in easily, I promise.”

He groans like I’ve just offered him something filthy and precious.

He pushes into my ass slowly. The stretch burns a little first, as always, but the oil makes everything so slippery that he is soon buried deep. He starts fucking my ass in steady strokes while the other man holds my head and fucks my throat again. I come like that — hard and sudden — my whole body shaking between them. Another man takes my arse after the first one finishes inside it. Then another. I lose track of how many times I am flipped and repositioned. Every time a new cock pushes into me somewhere, I make soft, eager little sounds. I love how different each one feels. I love being passed around like this. Then there’s a little break in the action. All but one of the men step back from the table. I hear drinks and ice, but I still have someone to please, so I focus on him.

He’s a tall, broad man with a thick cock and big hands.

He climbs onto the table and gently takes hold of my ankles. He removes my Mary Janes one by one, then slowly peels the little white socks off my tiny feet. He scoops a large handful of oil from the pool around my body and starts rubbing it thoroughly into my bare feet. His thumbs press deep into my arches, then between my toes. It doesn’t tickle, but it’s strangely intense. I watch him with wide eyes, then I start to help — flexing and curling my toes, rubbing my oily feet together for him. He’s my first foot guy, it seems.

He comes a little closer, his rock-hard cock twitching. He wraps both of my feet around it and starts fucking between them. I love it. I move them for him as he grips my ankles tight, pressing my soles together, stroking up and down his shaft. It is so new, so fucking intense — just the two of us under the bright light while the others watch this strangely intimate moment from the darkness. “Come for me, Daddy,” I whisper.

He ups his pace, holding my hips tight, then he groans and comes hard, thick spurts landing across my toes, my ankles, and the tops of my feet. I keep moving my feet gently through it until he’s completely spent and lets go of my ankles.

“Thank you,” I whisper. He strokes my calf once before climbing off the table. “No. Baby. Thank you.”

The others soon come back after that. Two men stand at the head of the snooker table and hold my wrists above my head while two more spread my legs wide and hold my ankles, stretching me out completely on the slippery rubber. I can’t move, not that I want to. One of the men climbs onto the table and straddles my chest again, pushing my oily breasts together and his cock between them. He fucks them while another man fingers me fast at the same time. When they are done with that, and there is even more come coating my chest, they flip me again, onto one of their friends.

I end up on top of him, on my back with my legs pushed right back against my chest. They slide me oily body down him, impaling my ass on his cock. They move out of the way quickly, and before I can moan my pleasure at being taken in the ass again, another cock slides into my pussy. The stretch is intense, and I scream, but I love it. They fuck me together, holding me in place while I slide and slip beneath them. They both come, and abandon me there alone, leaking and used.

I get a few minutes respite, and assess my situation — I am such a mess, the cute headband has gone, the dummy has also disappeared, I’m lying on my side in a pool of oil and sweat and come. My hair is soaked with all of it. I hear Papa’s voice. “You’re doing good baby. Can you handle some more?”

“Always, Papa,” I say into the darkness. And I mean it. I’m tired, yes, but the oil has done a fantastic job of preventing any soreness, except maybe in my throat, but I’m used to that now.

I don’t look up as bodies surround me again. A man lies beside me, and I am lifted onto him and lowered onto his cock to a satisfying squelch from my pussy as I straddle him. I lift my head. “Hey, daddy,” I say as I begin to ride him. “Your cock feels divine.”

A guy climbs on behind me and pushes my body down onto the guy I’m riding. A filthy idea hits me, and I look up at him with big, hopeful eyes.

“Can two of you try to fit in my pussy at the same time?” I ask softly. “Please, Daddy?”

The men around the table make low, approving sounds. They make it work.

It takes some careful positioning, but eventually, I have two thick cocks stretching my pussy wide at the same time. The feeling is overwhelming — so full I can barely breathe — but I love it. I come harder than I have all night, sobbing and shaking while they hold me still and keep fucking me.

By the time the last one is finished with me, I am completely exhausted.

I lie in the middle of the table, legs loosely spread, chest heaving. Oil, sweat, and come cover almost every inch of me. My hair is soaked and sticking to my face. Come is splattered across my breasts, my stomach, my face, and leaking slowly out of everywhere it can. In my daze, the dummy has been gently placed back between my lips at some point, tasting of whisky again, and I am sucking on it without thinking. It’s soothing, as is the whisky on my throat.

Gregory steps into the light above me. He looks down at me — a slippery, used, blissed-out mess — and reaches out to stroke my cheek with his thumb, not caring about the mess.

“That’s a good girl,” he says quietly. “Was that fun?”

I blink up at him dreamily and nod around the dummy. He takes it and tips it in his drink and presses it back to my lips.

From the darkness around the table, I can still hear the men talking softly.

“Look at the state of her… she’s amazing, Gregory. Keep her. Better still, let’s do this again.”

“Fucking incredible little thing.”

I close my eyes and suck on the dummy, floating.

I have never felt more used.

Or more content.

Hi! It’s P.T. I do hope you are enjoying this story. Did you know that we writers thrive on your feedback? — You can clap up to 50 times (please do), highlight your favourite passages, and I love reading your comments. It helps our work be seen and also helps us grow as writers.

[embed]List: Leah and the (much) older man | Curated by P.T. Brown | Medium Leah and the (much) older man · Eighteen-year-old Leah meets a handsome older stranger on a park bench, and her sex…medium.com