Apologies for any typos. Wrote this on my phone with one hand. All my stories are real though I edit the dialogue to cut out the boring bullshit. Enjoy
Maddie was a friend of a friend. 5’10” long brown hair with a slim thick body type she had some amazing legs and ass. We got setup on a date and had a good time going to dinner. We made out after dinner with me getting to squeeze her ass a bit but nothing more. 2 nights after dinner I text her asking if she wants to go out again and she lightly lets me down saying she’s too busy and doesn’t think we’d work out. I shrug it off and move on to the next girl.
A week or two later she texts me asking if I had any super bowl parties to go to. I let her know I was attending my buddies and she was free to come along, an offer she eagerly accepted. When it was time, I picked her up from her apartment. She was wearing jeans and a crop top and gave me a hug, pressing full tits hard into my front before hopping in the car.
Despite telling me she didn’t want to date or hookup before, Maddie was extremely flirty at the party. Once the game ended we walk back to my car. She ends up jumping ahead of me and I can’t help but stare at her ass as she walks. She must have known i was looking as she starts swaying her hips back and forth. I can feel my cock growing hard in my jeans as I try and push the thought of her bent over out of my head.
“She already rejected you dumbass. She just wants to be friends” I think to myself as we hop into the car. I sit down and turn the key, looking at the mirrors as I hear Maddie speak
“Did watching my ass do that?”
I can feel my face turn hot and red and blood rushes to it
“Do what?” I ask nervously as I turn to look as her. She’s biting her lip as she looks at me reaching up to tuck a strand of hair behind her ear. Maddie leans forward, across the center console as she reaches out with her right hand.
I can feel her hot breadth on my lips as her fingertips lightly touch the top of my hard cock
“This” she answers before I lean in and start kissing her. I start off with the intention of going lightly and teasing her but our lips have barely made contact before I can feel her tongue invade my mouth. She was hungry from me and her fingertips were suddenly replaced by her hands as she grabs onto my cock and starts squeezing. We make out for a minute or two as I grope her d cups over her bra, before I push her back in the seat breaking the kiss.
I lean back in my seat and quickly pull out of the parking spot and start driving back to her apartment.
“You know” Maddie says in a singsong voice I hadn’t heard from her “I don’t know why but I trust you fully, you can do whatever you want to me.”
My mouth kinda drops open for a minute as my mind surges with the possibilities. “What do you like?” I ask her as I reach over and grab her wrist, placing her hand back onto my cock. I grab her other hand and push it towards her pussy. While she grabbed my cock instinctively she didn’t do anything with her other hand.
“I don’t have” she stutters out “I don’t have much experience. Ive only had sex a few times with my ex” she says nervously. I can’t help but let out a little groan, my cock twitching. I’d done very well in college but almost all with sluts, I didn’t get to fuck many inexperienced women.
I push her limp hand back onto her pussy “rub it for me, we will be back to your apartment soon and I want it nice and wet.” Maddie slowly started rubbing her pussy over her jeans as I drive, her hand squeezing and stroking my cock through mine. I pull up to a red light and give her my attention for a moment. Leaning in and kissing her as I reach around and pop her bra open before playing with her tits through her shirt. I can feel her breathing change against my mouth as I grab one her big tits and I smile, seems I found a sensitive spot.
I lean back and keep driving, making out and playing with her at every red light. I roll her nipples around on my finger, feeling them get harder and harder against my fingers as she moans and leans back in the car.
Soon we arrive at her apartment and she leads me inside. I go to the bathroom to freshen up, walking out to find Maddie in just her panties kneeling on a pillow at the foot of the bed.
I walk slowly up to her as she bats her big beautiful eyes at me, lips slightly parted as I push my thumb into her mouth. She sucks on it lightly as she reaches up and undoes my belt and unbuttons my jeans. I pull my finger out of her mouth as I push my jeans down and step out of them, quickly yanking off my shirt in the process, leaving myself in just my underwear.
She bites her lower lip as she looks at my cock, pressed hard against my tight boxers, reaching out and rubbing her hand against my clearly outlined mushroom head
“I trust you.” She says
“What do you mean?” I ask her
“I’m not very experienced but I trust you. Do what ever you want” She responses as her hands grab the waistband of my underwear and pulls down. She lets out a moan beneath her breath as my cock slowly becomes visible until the underwear passes over the tip, causing it to spring out and smack her in the cheek with it. She laughs as she stares at it before slowly sucking on the tip. I don’t wait long before I push her back slightly, pressing the edge of her head against the bed.
“Relax” I say as I start to push my cock in to her mouth, slowly going farther and farther. She only gets about half of me down before coughing. I pull out, rubbing the head against her cheek, leaving a line of spit before her big brown eyes looked up at me. I hold her eye contact as I slide back into her mouth and push into her throat
“You can do it. Take that cock” I tell her while pushing back in. I manage to make it slightly farther before she coughs again. This time I only back up a little before pushing back deeper into her throat, repeating the process till I’m fully fucking her face, spit rolling out the sides of her mouth, my balls wet from spit as the smack her chin.
I pull out her mouth and look down at her. “Enjoying yourself?” I ask her as she recovers, eyes slightly glazed over.
Maddie nods, a “yes sir” breathlessly passing from her lips. My cock twitches, I fucking love when ladies say that. I reach down and pull her up by her armpits and shove her down on the bed. She lands on her back and I grab her under her knees, spreading her legs around my hips. I release her right thigh and slide my finger along the center of her panties.
“Fuck you’re soaked” I let out feeling the wet silk before hooking my finger under the edge and lifting them up and to the side. I run a finger up and down her meaty lips, circling her clit with my thumb as her moans increase in volume. I glance up at her face , her eyes closed as she open mouthed moans and squirms under my fingers. I continue to rub her clit as I bend knees. My left hand slides a finger inside her pussy, enjoying her tightness for a minute before I rub her wetness over my purple mushroom head. I line myself up as I tease her, just barely pushing the tip in before pinching her clit and sliding all the way in at once
“Oh fuck” Maddie let out in a high pitched moan. I keep my cock buried to the hilt in her, flexing it as my fingers strum her clit. “Oh fuck oh fuck oh fuck” she moans out as I continue. I can feel her pussy tightening around me. Her moans turn into a squeaking noise, getting quieter and quieter as her pussy gets tighter and tighter. I slowly slide my cock out to the tip as I slow my fingers keeping her just on the edge until my cock nearly pops free before shoving myself back in and moving quickly on her clit.
All of her muscles spasming as she cums around me, pussy clamping down hard before I feel a rush wetness. I fuck her slowly but deeply as she recovers, waiting for her face to change back from the deep shade of purple that had arisen. After a few minutes I could feel a slight tightening in my balls and knew what I wanted.
“Hands and knees” I commanded her as I slide out, Maddie shakily turned obviously still not fully recovered from her orgasm. She got into a doggy style ass hanging off the edge, her inexperience showing. Her back was straight and she had most of her weight on her knees.
“Relax” I pull her ass into the air and push her face down into the mattress pushing down on her lower back “keep this bend” I say as I slide back into her. I slap her ass hard as I start to fuck her, giving her a moment to get use to the angle but quickly turning into hard fucking, enjoying the sight of her fat ass bouncing against my hips. The tightening increases as I start to get louder, moaning and telling her how good her pussy feels.
“Oh fuck” I grunt out as I can tell myself hit the edge, slamming my unprotected cock as deep as it can go before exploding inside of her. I can feel rope after rope filling her as I hear her mutter a slightly scared “oh fuck” from underneath me.
Once I finished cumming I pulled out, enjoying the sight of a stream of cum leak out of her cunt after me.
Maddie ended up telling me after that she wasn’t on birth control so I bought her some plan b. We ended up hooking up a few more times but wanted different things
Source: reddit.com/r/gonewildstories/comments/si5bhu/mf_inexperienced_maddie_gives_me_cunte_blanche
Great story.