I have a love-hate relationship with copious backstory/lead-up so I’ll try and thread the needle here.
The events of this story transpired on a night during the summer after I graduated high school, but I should back up a little first. From sophomore to senior year, I had dated a girl named Jenn. I loved Jenn. We had a fun and vibrant relationship that seemed like it would never end. Not too long after we began dating, we took each other’s virginities and proceeded to fuck constantly for the next 2 years. I had more sex in that time than any other 2-year span since. Trojan stock soared…but then it ended. I’ll spare you the gory details of why the relationship ended, but let’s just chalk it up to her suddenly wanting something else shortly after the start of senior year. High school shit. It wasn’t until we were done that I realized just how lucky I had been with respect to Jenn’s body. Imagine a volleyball player. Tall. Long, thick thighs. Flat stomach. Respectable breasts. Long blonde hair. But most of all, HUGE ass. I was absolutely obsessed with her ass. Still kind of enamored with it to be completely honest. Suffice it to say that we fucked doggy style a lot. I’d say Jenn’s celebrity doppelganger would be a tall, and even curvier Amber Heard. To this day, any time I see a woman with Jenn’s body type I can’t help but stare. Pavlov’s dog.
Anyway, I spent the 6 months after our breakup ‘dating’ a few girls here and there but never really being interested enough to go past hooking up. I even had a Friend with Benefits for a short period, but that’s another story. I spent most days missing Jenn’s body. Remember, this was high school, and Jenn and I remained friendly, so I had to see that ass every fucking day until graduation. It was torture. Constantly in yoga pants, always haunting me. I don’t think I was necessarily missing Jenn I guess I just missed getting to fuck her all the time. And seeing her walk down the halls wasn’t exactly helping, but I digress.
Fast forward to the middle of the summer after graduation. A well-to-do friend’s parents are in Europe for 2 weeks and there’s a going to be a huge party that everyone is going to be at. I had a job for the summer that I left around 8pm, so I’d be late, but I wasn’t going to miss a chance to get fucked up with everyone. I always hated showing up to parties sober, so I sat in my car outside of the house for a few minutes taking pulls from a flask of my dad’s whiskey (I was also a fucking idiot). After I get a sufficient buzz going, I walk up to the house and open the door. Mostly everyone there is either drunk or well on their way. I spot my friends in the kitchen taking shots at the island and I proceed to go up to them and join in. After about 15 minutes of drinking and laughing with everyone, I decide to check out the basement. There’s music playing and everyone’s having a good time either dancing or standing around talking. Not long after being down there, I hear someone shout my name. Of course, it’s fucking Jenn. She’s wearing a red summer dress I recognize because I always loved how it showed off her assets. She walks up to me with a wave, says hi and tells me she’s so happy to see me as we embrace in our first hug in a long time. I think this may have been my first time seeing her since graduation. I tell her I’m glad to see her as well and she begs me to come take shots with her. I’m buzzed already and I can smell the Svedka on her breath but I think ‘fuck it’ and allow her to grab me by the hand and practically drag me to the corner of the basement where she’s stashed her alcohol.
We take a couple drinks and make small talk. She’s flirty and smiling at me constantly. I chalk it up to the alcohol and forget about it. She asks me to come and dance with her and I say, ‘Sure why not.’ She leads me to the impromptu dance floor and we dance. God damn, do we fucking dance. We fall in to our old habits quickly. She begins by turning around to face me, looking at me with a smirk, and laces her hands around my neck. She’s grinding her hips in to me. I’m grinding right back. My hands begin on the small of her back, but they don’t stay long. She smiles widely as I slowly moving my hands to her ample backside, pulling her even closer to me.
She puts her cheek to mine and says in my ear, “You always did love my ass.’
‘Can you blame me?’ I respond.
We dance to the end of the current song and in to the next. Suddenly, she turns her body around and she’s grinding her ass in to me. It’s at this point that my dick starts to wake up, alcohol be damned. I missed the feeling of her body on mine. I missed running my hands all over her. This felt so familiar and yet foreign at the same time. I run my hands up and boldly grasp her C-cups. She looks back towards me and has an extremely amused look on her face. I lean forward and kiss her hard on her soft pink lips. I missed those too. Her grinding slows even further and her tongue finds its way in to my mouth. My hands are still on her tits and her ass is still moving up and down on my dick. We stand like that for what seems like a long time. I didn’t even care if other people saw (they did).
She breaks away suddenly and takes my hand. We all know where this is going. This is her best friend’s house so she knows the layout very well and she begins leading me to the third floor. We go up two flights of stairs and she makes sure to give me a good view both times. On the first flight up, she lifts the bottom of her dress just a bit so I can see where her legs turn into ass and I catch a flash of her pink thong. A thong I recognize as one of my favorites of hers. She knows this and smiles even wider. On the second set of stairs up to the top level she stops abruptly and turns around. She grabs my dick through my pants and I am instantly hard.
‘I can’t tell you how much I’ve missed your cock’, Jenn groans in my ear.
And just like that, we’re moving again. She takes a right at the top of the stairs and opens the door to an empty guest room, holding the door open for me. I walk to the bed and she closes the door behind her, leaning against it and staring at me. She walks slowly towards me.
‘I want you so fucking bad’, she whispers over the distant music two floors down.
As she reaches me, her hands immediately go to my belt and her lips to mine. She has my belt and pants undone in no time. They’re old friends. Her eyes are glued to mine as she leans her body in and very slowly drops down to the floor, making sure I can feel her tits graze my dick. That’s where her eyes go next. She grabs the waistband of my underwear and hesitates for a second
‘You switched to briefs.’
I chuckle. ‘I guess I felt like I needed something more mature than boxers’
‘I like it’, she says, breathing heavily.
She slowly lowers the waistband and frees my cock. I’ll never forget the sight of it rock-hard dangling over her face as she stared at it, even if it wouldn’t be the last time. She’s on it in a heartbeat. She took as much of my length she could fit into her mouth at once. I moaned loudly as she began to massage my cock with her mouth. I missed the sight of her pink lips wrapped around me. She maintained eye contact with me the entire time, sucking hard and making sure to cover my whole dick in her warm saliva. I almost lost it as she took me into her throat and held it there, making light gagging noises. I couldn’t take much more of this. I pulled her off and brought her face up to my mouth, kissing her hard.
‘I need you out of that dress, Jenn’
‘Yes, sir.’
She stood up and turned around. She lifted her hair and leaned back, meaning for me to unzip her dress. I obliged and got more excited by the second as I slowly revealed her soft, lightly tanned skin. She was wearing a pink push-up that did wonders for her already beautiful tits. As the zipper reached the end of its journey I was finally granted a full view of that pink thong I had spied minutes earlier. As the dress fell to the ground I could have cried at the sight of her fucking glorious ass. I grabbed it hard and she leaned back in to me. She turned back around to face me and started unbuttoning my dress shirt.
‘I can’t wait to have your dick back in my pussy, baby’, she whispered.
‘I can’t wait to hear you scream my name as I fuck you’, I responded.
‘Fuck.’
After she said this, I scooped her up and had her laying on the bed in less than a second. I moved on top of her and kissed her deeply, once again exploring her mouth with my tongue. I broke away and slowly kiss my way down the length of her body. Finally, I reach my destination. I separated her legs and kissed her pussy over her panties. Her G-string was soaked already. No foreplay necessary. I pulled her panties to the side and immediately licked the length of her pussy. She moaned loudly and ran her fingers through my hair as I looked up at her, my tongue pressed to her clit.
‘Fuck, baby’, she whispered.
‘You’re so wet for me, Jenn,’
I wasted no time. I ate her pussy like never before. I fucked her with my tongue as I rubbed her clit. I then switched to fucking her with two fingers and sucking her clit. She practically screamed the entire time and pulled my head towards her soaking pussy. She came extremely hard after a few minutes and wrapped her legs around my head as she rode out her orgasm. After she came back to reality she pulled me up to her face and we kissed again for a few minutes as she tasted herself on me.
‘Please fuck me, please fuck me’, she started to beg between kisses.
I couldn’t wait any longer. I leaned off the bed to grab a condom from my pants and Jenn removed her bra. As I fumbled with the package, she grabbed it from me and threw it across the room.
‘No, I need to feel you baby.’
Was it stupid? Yes. Do I regret it? Not really. This would be the first time I fucked Jenn with no condom, and I couldn’t fucking wait. I positioned myself above her and practically ripped her panties off. She was grasping my forearms and grinding her pussy up towards my dick. That look of pure desire in her eyes and the sight of her laying there naked right before I plunged into her is one of my go-to memories. I rubbed the head of my cock up and down her pussy and she sprung in to action. She took my dick in her hand and slowly pushed it in herself before I could tease her further. Her mouth opened and she moaned as I penetrated her. I slowly dropped to rest my weight on my forearms. I took a second to just lay over her and appreciate the feeling of being inside of Jenn’s pussy raw.
‘Fuck I forgot how good you feel,’ she said in amazement.
I began to thrust into her slowly. I still remember how wet she was and how warm her pussy was. I built up momentum and we were soon properly fucking, Jenn moaning with every thrust. I kissed her as I rammed in to her and she scratched down my back with her nails. After a minute or two Jenn wrapped her legs around me and I felt her pussy clench as she came on my dick. I saw her mouth open as she climaxed but no sound escaped.
‘FUCK!’ she said loudly as her body finally relaxed.
I continued to slowly thrust in to her and she pulled my face down and kissed me.
‘I want you to fuck me from behind,’ she whispered.
I didn’t need to be told twice. I quickly flipped her over and positioned myself behind her. She got on all fours and offered her pussy and ass to me. The sight of her with her face down and pussy in the air is one I cherish greatly. I again wasted no time in moving behind her and grabbing her huge ass as I plunged into her pussy again. I was ramming her pussy in no time. I couldn’t slow down. I grabbed her by the hair and used it to pull her head back as I plowed in to her repeatedly. I know I said I loved fucking her doggy style but believe me when I say she loved it too. This time she was practically screaming as we fucked.
‘Fuck me. Fuck me. Fuck me.’ Jenn said with each thrust.
I wasn’t going to last much longer. Her pussy was so wet and tight and I couldn’t believe how good she felt with no condom.
‘Fuck Jenn, I’m going to come,’ I told her.
‘Come inside my pussy, baby. I want your cum so bad. Please fill my pussy.’
Holy shit. To this day, the hottest thing I’ve ever heard. As I continued to fuck Jenn as hard as I ever had, I didn’t even think. In less than a dozen strokes, I exploded in her pussy. I coated every inch of her inside with my cum. It felt like forever before I finally emptied everything in to her.
‘Oh my god, baby. You filled me up’ Jenn said between gasps for air.
I pulled out and a ton of my cum rolled down her leg. She collapsed and pulled me on top of her. We made out for a long time. After a while, we fell asleep. When we woke up in the morning, we talked and joked around about what had happened. We agreed not to tell anyone. Then we went our separate ways.
Source: reddit.com/r/gonewildstories/comments/6j61cj/the_night_i_came_inside_of_my_ex_girlfriend
Do you really think that briefs are more mature than boxers
I appreciate that this is the thread of conversation after the story.
Also, great work OP.
Wonderful writing. I was mesmerized from start to beginning. If you have any other stories please share!
Really hot story! I agree, when a girl says those things, I lose any sort of restraint or willpower to last longer
This was really fun AND hot… fucking at a party, raw, with an ex? Sign me up! ;)
I never really understood how when two people who have strong lasting emotional and physical ties to one another can get back together for a fling and then without further explanation they separate again. It would seem to me that this has all the potential elements of a lasting and loving relationship and needs to be explored more fully by both parties. Doesn’t anyone know how to be happy anymore?
Nice! This is very hot!
There is NOTHING sexier than a woman asking to be filled with cum. Nothing…
Well, 2nd only to actually cumming inside a woman.
Well done good sir, i tip my hat to you
This is a super hot story! You’re lucky to have a Jenn in your life