Milfs Teen Conquest

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39 year old Milfs end.
6.5k words
4.65
36.4k
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Part 1 of the 5 part series

Updated 06/11/2023
Created 08/07/2022
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Yesok1
Yesok1
487 Followers

After my long journey, I pull my Audi into the drive of the holiday cottage that I've booked for the next 7 nights. The drive here has been too slow and arduous, and I'm looking forward to seeing my younger lover.

I've been seeing Izzie for 6 months, it's fairly casual and she loves sex. She loves fucking me as much as I enjoy being fucked by her. She's different to the other girls I've met, and this is why I have been seeing her for so long.

Getting out of the car, my red heels crunch in the gravel. I get out and walk around to my boot and pull out one of my two cases. I leave both my walking and riding boots where they are and plan to come back for the other small Gucci case in a minute.

The air here is fresh, though the summer heat is warm and dry, it's nicer than the London air as it's fresh and clean. I check my watch and see its 5.30pm. I could have got here for 4pm, but I had a late start and got stuck in traffic.

My daughters are both home from uni, and I had to make sure there was food in the cupboards and that they'd be set for the seven days without me. They'd kill me if they knew my girlfriend was only 18. She's younger than them both.

Izzie and I matched on a dating site. I travel to see her, taking her on trips to other hotels where it is unlikely that anyone will know us. Most of our dates take place in cities and hotels around the country.

We both flew out to berlin two weeks ago, regrettably, we didn't see much of the city, as we stayed in the room mostly shagging. Izzie will be here for two nights; I've only invited her for part of the stay on this trip as I'm concerned I will spend the whole week doing nothing but getting nailed by her and her strapon.

I use my strength and lift my case out of the car to drag across the drive to the key safe. I find it on the floor by the electric metre. The code 1467, makes the little door flip open. Dread fills me, as I notice there is no key.

Panicking I ring the doorbell, hoping that someone is in, but relief soon washes over me as a silhouette of a person passes the glass panel in the door. I scream with delight to see Izzie there as she opens the door, and she too squeals and puts her arms around me.

"You're here." I say surprised.

"I wanted to surprise you." She grins. She looks stunning, a white tracksuit top that is rolled up her fit tummy, tight ripped jeans that are high on her fit waist, and a pair of box fresh white trainers. Her long brunette hair hangs loose behind her.

"It's a lovely surprise, thank you." I answer. We pull my suitcase in over the door step and I kick my heels off.

"Thanks for inviting me." Izzie smiles. She takes my hand and leads me to the bedroom.

She pushes me backwards onto the bed, and my legs part. Her hands reach my ankles which she puts on either of her shoulders. We look at each other, silence and apprehension fill the room, and her hands slide quickly down my thick white legs. She immediately snatches at the waistband of my knickers and she soon heaves them along my creamy thighs, over my knees and flings them off into the corner of the bedroom somewhere.

"No chance for a lady to rest?" I say, a little shocked by the onslaught. A wicked smile flashes across her face, her eyebrow raises and arches as my fanny flutters in anticipation. I love her young face showing her delight in seeing me on my back.

My feet are now perched on the bed and I see her head drop between my knees as kisses trail down the insides of my thighs.

"I love your juicy middle aged cunt." She breathes huskily and I moan loudly and clutch the duvet as her mouth envelopes my fanny.

Her tongue draws shapes on my inner lips and she sucks my clit as the wetness builds.

"Oh my." She murmurs as she delves deep into me with her tongue.

"Oh my." I repeat thrilled at the young ladies actions.

"I'm going to cunt fuck your fucking face." I shout at her.

My short dress is rolled up around my waist. The small rolls of fat on my stomach are hidden under the fabric. At 39, I realise I'm losing my battle with my metabolism. I go to the gym, but I'm a prime milf with curves. I'm not so embarrassed or ashamed of my thin rolls as I was at our first meeting. Izzie says she loves my look, she's fantasized over her mums friends and the mothers of her own friends for years.

I look at her as she smiles at me with a mouthful of my cunt. I lift my arse from the bed and grind my pussy onto her face. Her hands clutch at my fat arse, she gently squeezes it and I feel her drag her long nails across the soft dimply skin of my arse.

Her tongue works it's magic probing my pussy hole. She tongue fucks me, and I squirm at her wet muscle moving in and out of my vaginal ring.

I clutch the duvet and moan with lust as I quickly cum into her mouth.

"You're in for a fucking tonight." She says unzipping her top, she pulls it off, and then hurriedly followed by her short, tight vest top. Her thin fit body looks beautiful and youthful. Her small tits push at the fabric of her pale pink bra. As her bra pings off, her nipples stand erect.

She lies over me, pushing her nipples into my face as I stroke and play with her hair and her back. I suck her delectable tits, as she cradles my head with one hand and holds the headboard with the other.

Glancing up, I see her watching me, getting off on me sucking her breasts. Her large hooped earrings hang down next to her cheeks. Her pink bubblegum lipstick makes her lips look so kissable.

I sense her kick her shoes off with her feet and she quickly kneels with me between her legs. She looks excited as she undoes her top button of her jeans.

"Hang on for a minute." She grins and jumps off the bed. She pulls her jeans off over her white arse, and the black thong follows her jeans down to the floor.

Opening her small case she pulls out her strapon. Expertly pulling it up her legs, she buckles it quickly and gets back onto the bed.

It's not long before I feel the big head of the dildo push at my fanny lips. My soaking cunt allows it to force itself into me with the width of the plastic cock parting my cunt walls. I feel it slide and stretch me.

"Fucking hell." I complain loudly.

Izzie laughs, "Its a new one. I thought your hungry cunt wanted something more fulfilling!" She watches herself press the snake between my legs.

I fling my head back onto the pillows, a shallow scream of pleasure escapes my throat.

I feel her body press into me, holding my knee and waist, I'm bewildered to feel the thick shaft slide quickly out.

Izzie's hair hangs over her face, but I can see her smile, and concentrate as I squirm with delight below her. Her pace is starting to pick up as my cunt accepts her rogering, as the 18-year-old lies over me, her arms extended with a hand just under both of my arm pits.

Her cock now is held just inside my entrance, and she nods down to kiss me. "Hold on tight." She says.

My head spins as she starts hard fucking me missionary style. My ovaries are being smashed and my womb is being thrust up into my rib cage. I'm sure my spine will be ruptured if she hammers me any heavier.

The slapping of her motion into my hairy wet gash, is noisy. My vocal pleasure must be heard down the street as I feel like I'm being pounded into next week.

Thank God I'm not planning on having more kids, I'll be ruined by the time she finishes with me. Running my hands down her back, I feel her perspiring. We pant together as her persistent pace is relentless.

I'm relieved as I feel my orgasm build and she squeals as I dig my nails into her, they drag as a reflex to my coming scratches red lines down her sides.

We both melt into a heap and hug. Exhausted from the drive and worn out from the sensational fucking.

Suddenly and unexpectedly we're disturbed by the doorbell ringing. A little argument ensues about whether I should answer it. Izzie thinks I should leave it, but I say it's polite to get it.

I get up, and my cunt sucks at the contraption as I remove it from within me. I pull my skirt down, it feels wet from pussy juice, and I feel a little sore as I walk. I look at myself in the mirror and quickly reshape my dark hair. The bob haircut hangs looking the post shag mess that it is and I quickly try to reshape it with my fingers.

"What are you doing?" Izzie laughs at me as she lies naked bar trainer liners on her feet and a fairly big prosthetic dick between her legs glistening with my cum.

"Making myself look presentable." I reply. I purse my lips and try to reshape the smudged rouge lipstick.

"You don't know them, you shouldn't worry how you look." She counters.

"Its my self respect honey. I don't want to look messy. I want to look nice for whoever it is." I explain.

"You look fucking hot, to me." She answers.

"I might, but whoever is at the door isn't there to see someone messy, looking just fucked, they don't expect that." I reply. I see her shrug. "Get ready for round two, I will be back." I add.

"Yes, Mrs Oakley." She grins. I'm focusing on my cheeks but my eyes dart to her. I hate her calling me that, but she does it for her own gratification, I know she's teasing me. I shake my head and smile to her. The doorbell sounds again.

"Open the windows, it's warm and it smells." I say straightening my dress to go to the door. "They're open already." She whines like a brat.

I get to the door and open it, seeing a young woman, probably mid thirties standing on the step holding a basket.

"Hello you must be Jess?" she says holding out a smart manicured hand. Her nails are painted, and she has little diamontes inlaid into them.

I shake it and say hi a little confused.

"I'm Tracey, we've been talking on email, you made your booking with me." She smiles, her dialect is strong local sounding. I laugh a little internally imaging her to be a pirate with her accent. I wonder if she'll start her next sentence, "ooh aah, me hearties."

"Of course, thank you, it's a lovely place here." I smile at her and relax a little as the penny drops.

She hands me a basket. "I've got a little local produce and a bottle of wine to welcome you."

"Thank you, that's very kind." I smile at her glancing at the baskets contents.

"I was wondering. We've had a couple of issues with the boiler and hot water. There shouldn't be a problem, but if there is, would I be able to show you a quick fix to put it right. It will save you any frustrations." She smiles and looks at me. "It's just in the kitchen, may I?"

"Absolutely, of course." I say as I step back and allow her space to enter.

She walks to the kitchen. "By the way. I wouldn't play music too loud or have the tv volume up high, it's a quiet neighbourhood, and people have a tendency to complain." She's hesitant as she says it, and she flushes a little pink.

"Music, tv?" I say confused.

She winks at me, turning a little redder. "err, you and your husband..." she says quietly.

"Husband?" I repeat. She looks a little awkward, and I feel confused. She opens the front of the boiler that's in a cupboard and starts to explain what I need to do. She's pointing and directing me, but I'm half looking at her arse in her running tights and her white pointy ankles, just above her Nike trainers.

Izzie walks in, she's braless but has pulled on her vest top. Her nipples press at the ribbed fabric. Two small gold chains hang between the small mounds of her breasts, her gold hooped earrings dangle motionlessly from her ears and just in front of her hair. She's put on shorts, she's barefoot, and her legs look long and amazing.

Tracey turns her attention from the boiler to Izzie. Izzie looks full of attitude and pissed off at us being interrupted. She says a hello, and leans against a counter watching, arms folded across her midriff.

"You must be Jess' daughter." Tracey smiles.

I feel embarrassed as a flash of anger crosses Izzies face. I interrupt, to stop any fierce or aggressive reaction from Izzie. She's a hot head teen. She feels as though the world owes her something and hates people assuming. I have tried to explain and talk to her about peoples personal beliefs and the inherent judgements they make rightly or wrongly, and it's nothing personal being directed at her.

I see it in my daughters too, to a lesser extent, but the worlds changing from the one I grew up in. There is an expectation that people should be kind, and I find at times Izzie and my daughters can be cruel if people don't share their beliefs.

"Sorry." I say to Tracey. I smile a little, plucking up courage, and trying to make her feel comfortable. I reach for Izzies hand who grabs mine forcefully. "This is Izzie. She's my girlfriend." I continue.

Tracey looks very apologetic and even more embarrassed. She looks at Izzie who scowls at her a little unkindly.

"It's ok." I reassure her. Izzie tuts. Tracey finishes showing me the boiler and tries to make a quick escape. I try not to laugh as she trips over her words, I want to stroke her arm or hold her hand and tell her not to worry.

Izzie laughs as Tracey falls over my suitcase by the front door. "Enjoy your stay, it was nice meeting you both." Tracey says. She fumbles at the handle but the door won't open.

"I think it needs to be unlocked with the thumb key." Izzie cruelly laughs, I elbow her hard in the ribs.

"I know." Tracey turns and unlocks the door, she can't get out quickly enough. I go to help her, thanking her and close the door behind her.

"Fucking daughter." Izzie shouts.

"Calm down. How is she to know?" I say calmly.

"That's insulting. You don't look that fucking old." She shouts.

"That old." I pout, "thanks!" I look down.

"Sorry." Izzie strides towards me and hugs me. "That came out completely wrong." She says holding me tight.

"Great fuck earlier. By the way, we might need to keep it down. I think she may have heard us." I tell her.

"What." Izzie says looking angrily at me.

"She made a roundabout comment about playing music or the tv too loudly, oh and something about my husband..." I add, I laugh internally knowing Izzie will get cross.

I see Izzie raises her eyes, I sense her fume. She goes back into the kitchen and looks at the basket. "I suppose this was nice of her." Izzie says picking up the wine. She puts it on the side and starts to put the breakfast things in the fridge.

I lean against the door frame watching her and then I step behind her and tug her shorts down.

"Oh hello." She says seductively.

"Let me see that cute little arse." I say nibbling her ear.

She wiggles her waist slightly and I bend down. My red finger nails are bright against the white of her arse. Her tanlines are obvious as her shorts drop to her feet and I open her butt cheeks. Her arsehole is small and beautiful.

Pushing my face into her, I breath in deeply through my my nose. She smells a little musky, and sweaty from fucking me earlier, or sitting on a train for most of the day.

She sighs as I lick her hole. It twitches against my tongue and she braces her arms against the fridge.

"Oh, Mrs Oakley." She sighs heavily again. As my tongue tickles her arse she squeals lightly at the sensation. I playfully smack her arse leaving a light hand print.

I push my tongue into her arse, as she presses back into me face, and I hold her hard. My tongue stretches, but her ring is tight, and it fights my intrusion. I've eaten her butt countless times now, I love how pert and tight it is. Her hole is like a safe needing to be cracked.

Izzie gasps as my tongue forces itself down her dry hole. She tastes more bitter, and gets moist the further in I get. I spit into it, and swap my tongue for two fingers of my right hand. My left arm draws across her chest and I hold her close squeezing her right tit roughly in my hand. Her arse is out and I fuck her hole with my fingers.

She squeals and squirms as my hand pistons in and out of her brown hole. The little hottie is dirty as hell and her arse clamps my fingers, making them sticky. My churning of her hole makes the room tinge with her aroma. I can feel the little beads in her arse scrape and rub my fingers that push up to the knuckle of my hand.

Izzie stamps a foot and she pushes the fridge back an inch or so. Her lovely hands and long nails tap the side of the appliance as she anally cums against my hand. My fingers feel clammy and a little mucusy as I withdraw them from her ring.

She turns to me and kisses me. Our noses presses and I feel excited to have such a gorgeous girl here with me. I only imagined her being an occasional fling, and that things would fizzle out after a few meetings, but we have a keen fondness of each other.

I turn to wash my hands in the sink, as Izzie closes the fridge and then puts her arms around me, she kisses my neck and ear.

"I really like you Mrs Oakley." She whispers.

"Stop it, don't call me that. Call me Jess, you make me feel old." I complain. "I've never been Mrs, and Oakley is my maiden name too."

"Ok Jess, whatever." She answers and pinches my bum. "So fucking sexy." She says before prancing off.

Shortly afterwards in the bedroom, we lie on the bed resting. It's quiet, I can tell something is bothering Izzie, but I don't say anything. After a moment or two she breaks the silence.

"Jess, can we talk?" Izzie gets serious.

"Absolutely." I smile at her and look into her brown eyes. She looks back at me and returns a big grin.

"Ok." She sits up crossed legged on the bed and plays with her fingers. "I've stopped seeing other girls. I tell my friends that I have a girlfriend. They ask about you, they've never met you. We travel, and I enjoy it, but..." she stops.

"...I suppose there's a number of things that bother me." She pauses and takes a breath.

I listen.

"Are you and me... You know... It's just that I feel..." she fidgets.

I don't interrupt.

"We're not equal. Sometimes I feel like your daughter. I'd like to pay for things, but it's always you paying, and I can't afford it. You're older than me, I feel, lesser, I suppose. My job doesn't pay great, and I don't want you thinking I'm taking advantage." She explains bravely.

"I honestly don't mind. We are equals. I'm fond of you. You're certainly not my daughter. I never think of you that way either. They'd kill me, I think..." I stop myself realising what I'm saying.

"Kill you?" she responds with a little alarm.

"They have no idea that I see women for sex. Actually, they have..." I say.

Izzie jumps in. "You see women for sex?" She pretends to be shocked.

"I do." I pretend it's a surprise.

"My kids have an idea that I'm gay. I need to have a conversation and I keep avoiding it. They found out about a previous relationship and have put two and two together. A friend hasn't helped with her big mouth either." I explain.

"Do you want me to help." She looks at me. I know she means well, but sitting with my daughters next to a girl younger than them won't be a help at all.

"Thank you, but not just yet." I smile. "You'll want to settle with someone younger than me. I'm happy as things are between us, but for you, I'm 21 years older than you. I was your age when I had my oldest daughter. When you're in your twenties I'll be in my forties, you won't want that, you'll want someone your age with your interests." I explain. She listens, and nods her head.

"I know what you're saying. But you're perfect to me, they'll always be the age gap, I'm happy with that, I'll mature as I get older. We could be happy together." She smiles. "As long as you don't trade me in for someone younger when I'm thirty." She says.

We both laugh.

"I was thinking. Wouldn't you want to go to University? You don't have to, but it could open more opportunities for you." I ask her, interested to see what her ambitions are.

She looks thoughtfully for a moment. "I would, I'd do history or geography, but I couldn't afford it. I don't think I'm intelligent enough." She sniggers nervously and looks to the ceiling before turning to me. She grins hesitantly. "I guess being a travel agent is the best I can be." She shrugs.

Yesok1
Yesok1
487 Followers
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