To skip to the sex: go to the break that reads “Flash forward: bedtime/tent”
Otherwise, enjoy my story!
My last few posts have been recent stories with my current girlfriend, but I wanted to circle back to some fun stories from high school/college. This seemed like a fun place to start!
I’ll set the stage very briefly just to get moving: Seven years ago…
I’m a senior in high school, and my prom date this year is a cute little red head. We grew up in the same school our whole life, but we never talked much until Junior year. Our relationship is pretty flirty for a while; there’s chemistry there, but I think neither of us was sure of how to go about those lustful feelings.
Flash forward: prom night.
I wear a tux because, let’s face it, it’s the only option for guys; she wears an incredible violet dress that shows the perfect amount of leg. Things are platonic at first, and we spend a lot of the night with our friends. That is, until the dancing begins. On the dance floor, she stays extra close to me, swaying her hips in front of me and lightly rubbing her ass against my pants. Not exactly grinding with each other – it wasn’t so overt – but rather a subtle, more discreet movement. This was a new step of flirtiness.
Flash forward again: leaving prom.
After a night of dancing and partying, we leave the prom and head back to the car to get to our after party. It’s our plan to go to our friend’s house to tent in her backyard and drink. I hop in the driver seat, and turn to see a wonderful sight. My date pulls her dress up over her waist, revealing a light pink pair of panties that hug her form incredibly well, and falls back into the seat. She turns and looks at me.
“What? I don’t want to ruin my dress.”
“Of course.” I say, believing that it maybe wasn’t intentional for her to flash me. Still, I think about that sight often.
Flash forward: the after-party.
Finally we arrive at the fun part of the night. My date and I get there around 11 o’clock because we had to stop to pick up my tent from my parents’ house. (This is also where we changed clothes quick; I into some sweats and a t-shirt, and she into a pair of leggings and an oversized sweatshirt.) By then, all of our friends had set up their tents in the main lawn, so I had to pitch mine on the side of the house not too far away. I should add that the plan was for her to stay in one of her girlfriend’s tents, and me in my own. I told my date to go say hello to everybody while I got the tent set up, and she scurried off to do so. This wasn’t the only tent I’d be pitching tonight. (<-Proud of that line.)
I finish up after about 10 minutes and head up to the house. By this point, my date had gotten started, and poured me 2 shots so that I could catch up. God, I don’t know how I drank like that in high school, but it somehow happened. I pick up the shots and throw them back, and inadvertently spill one all over myself. I’m embarrassed because it seems pretty amateur, but my date assures me it’s not a big deal. I run back to my tent to grab another shirt I had packed in my overnight bag.
In my tent with my shirt off, I hear the sound of footsteps by my tent. “Knock knock.” My date says, before poking her head into my tent. “Well well what’s going on here?”
“Oh, just cleaning up my stupid mess, as usual.”
“Oh…” she says, and steps into the entrance of the tent. “I thought you had to run away while you thought about that peek you got earlier.”
“What do you mean?”
“Oh you know…” she says suggestively. My date turns around and looks if the coast is clear, then promptly pulls her leggings down revealing those light pink panties I’d gotten a glimpse at earlier. “Remember now?”
“Uhh…yeah. I do.” I get a little awkward when someone comes onto me. It’s not something I encounter a ton at this point (though I’d already lost my virginity), so I’m not sure how to react to such an overt sexual tease.
“Good! Play your cards right, maybe I’ll show you more.” She pulls her leggings back up and stretches them over her ass, her panty line showing through the thin stretched material. She smiles at me, and then returns to the others. Tent two is pitched by this point.
Flash forward: party is winding down.
Not much happens while we’re socializing, but we spend a lot of time together playing drinking games, smoking a bong, and just being drunk high schoolers. Eventually I’m standing with my buddy, while my date chats with the friend she’s spending the night with. I glimpse over, still fantasizing about the rest of the body beneath those clothes, when I hear them start giggling. My date runs over to me, and my buddy takes the hint to disappear (I’d been telling him about our interesting encounters.)
“Hiya! I was chatting with Sarah, and she’s been trying to hook up with James tonight, so…I don’t know if I’ll be staying with her. I’m thinking that tent might be a little crowded for me haha.
“Oh man…I mean, you know you can sleep in mine if you’d feel more comfortable. It’s just me in there so there’s plenty of room.”
She bites her lip. “Yeah that sounds like a good idea.” She hurries back to her friend and they share another giggle together.
Flash forward: bedtime / the tent
Not too long after, the numbers at the party begin to dwindle down as most people begin to settle into their tents to either sleep or hook up. My date tells me she’s getting tired, and goes to grab her bag from the tent she was originally staying in. I head back to mine.
I desperately search my bag for a condom, but realize I didn’t bring one. I’m disappointed, but don’t give up hope. Maybe my friend will have one if I can just text him quick…
My date enters the tent. “Hiya!” She throws her bag on the ground and looks around the tent. “Lots of room, you’re definitely right. I have some bad news though.”
“Oh?”
“I didn’t bring a sleeping bag. Sarah had an air mattress, so I had planned to sleep on that, but currently she’s got a man on top of her on top of it, so I don’t see her willing to part with it.” She looks down and see’s my sleeping bag spread out. “Willing to share?”
“Yeah, we can make it work. Won’t need any other blankets with two of us huddled in there!”
I unzip the sleeping bag and climb in. Before I know it, my date pulls her leggings down and slips them off her ankles before joining me. She wraps her arms around me and throws her bare leg between mine.
“Hey…”
“Hi.” I say back. God I’m awkward.
“I…hope this is okay.”
“Of course it is.” I reply. I’m getting hard and I’m not sure how to feel about it. I’m sure she can feel it, but I’m starting to grasp that it’s probably expected.
“I’ve wanted to cuddle since we were dancing earlier.” She says, looking me in the eyes now. “We kept…brushing together. I wanted more.”
“I did too. It was nice dancing with you.” I say.
“Is that all you wanted to do? Dance?”
“Well…” I say, before she plants a kiss on my lips.
“I was tired of waiting for you to make a move.” She says, and then pulls my head in for a deeper kiss. We start making out, and my hands start to feel comfortable exploring a bit. First I slid a hand under her sweatshirt and held her breast in my hand. I’m unable to believe that I’m actually touching the girl that had basically been my sexual fantasy for the past 12 months. Before long I slide my hand out of her sweatshirt and move it down to her ass. I’m gentle at first, exploring how her panties shaped her wonderful curves. Then I squeeze her ass and pull her into me, placing my leg between hers so that my thigh rubs against her slit. Things are really heating up now, and any slow and methodical touching is out the door.
About 5 minutes of making out leads into her pulling my pants down. I’m still in my boxers, but we fish my sweatpants out of the sleeping bag. Then she flips her body around.
“Now this…” she says, as she starts to grind her half-naked ass against my now fully erect cock, “is what I’ve been thinking about since the dance.”
I reach around her and grab hold of her tit while I grind back against her ass. I start to kiss the back of her neck, as well as pinch her nipple, while we keep a slow but steady rhythm of sliding our bodies against each other. She’s breathing heavily now, and places her hand over mine while I feel her. Not long goes by before she slides my hand lower…and lower…and just beneath her panties. I can feel the stubble of recently trimmed hair.
“Please touch me.” She says. I move my hand a tad lower and feel the warm wetness of her pussy. With my middle finger, I gently slide between her labia to feel the juices coming from her, and swirl my finger around the entrance of her vagina. With my finger lubed up a bit with her wonderful juice, I slide back up and try to connect with her clit. It’s the first time we’ve hooked up, so admittedly it takes me a second to understand the feel of her pussy, but it doesn’t take long for me to find her clit and start rubbing it. I can tell when I’ve got it, believe me.
She starts grinding against me harder, rubbing her ass in different directions against my cock. I pick up the speed with my finger, and try to stay focused while also enjoying the heavenly tease I’m receiving myself. It’s too much for her eventually.
“Please fuck me like this.” She cries lightly, reaching her hand back and pulling my cock out of my boxers.
“I forgot to bring a condom.”
“That’s okay I did!” She says, and reaches into the pocket of her bag, removing two Trojans. “I can’t wait for you to make the move so I came prepared.”
I remove my hand from under her panties and take the condom. I take it out and slide it on my dick, enjoying the feeling. She pulls her panties over to one side of her ass.
“Please. Fuck me.”
I slide my cock along the outside of her pussy once, then I slip it in. She releases her panties and let’s out another small cry of pleasure, leaning her head back and pressing her cheek against mine. I start to thrust into her, returning my hand to its now preferred spot on her tit. We both breath heaving as I slide my cock in and out of her pussy steadily, enjoying every feeling we’re both experiencing. This goes on for about 5 minutes, before she turns her head back toward me.
“Hey!” She says, startling me a bit. “I said fuck me!”
I take things up a notch, by request. Without pulling out of her, I rotate until I’m now on top her her body, pronebone. I place my hands just above her hips, enjoying the incredible view of her tight, panty covered ass that I’m fucking. I thrust harder.
“Fuck me!” she says in a louder whisper. She’s demanding and it’s turning me on.
I push her down from the small of her back, and she in return lifts her ass a bit so I can fuck her even deeper. She moves her right hand beneath her body and starts to rub her clit while I continue sliding into her from behind. Her vagina starts to contract as she stimulates herself in all the right ways. I’m getting close; the combination of the view and the feeling. I try to keep up my pace, but I realize it’s going to be the end of me. It doesn’t matter.
As I’m just about to finish, she orgasms, and her tightening hole squeezes me straight out of her. She lets out one final cry of pleasure as she cums, her legs shaking and her hips collapsing back down. My ultra-stimulated cock comes out of her, and the only thing I can think to do is to press it between the cheeks of her ass. It slides in, and two or three thrusts later I’m cumming as well. She starts to giggle under her heavy breathing as she feels my throbbing dick mid-orgasm between her ass cheeks, filling my condom quickly. I collapse onto her, catching my breath for the first time since we started going.
“Well it’s about fucking time.” She says, still giggling.
“I’ll say…” I get out between breaths.
We lay in silence for a while, relishing in our post-orgasm bliss, and then fall asleep. Prom night was a success.
I wound up having some more experiences with this girl, but we never dated because we’d already selected our colleges by that point and neither of us was interested in long distance. If you liked this, I can share some more of those stories between stories of my current girlfriend and I. “The Chronicles of the Red Head with the Tight Ass.” Got a nice ring to it.
Source: reddit.com/r/gonewildstories/comments/tslcr3/mf_prom_night_shenanigans