Creaming my best friend and crush from 5 years ago [MF][cheating][LONG]

Don’t worry; the introduction starts in eighth grade, but the sex doesn’t start until we’re both over 18. We’re in college now.
If you want to skip the intro, scroll to the first line of ~~~~~ and start reading there. If you want to skip to the raunchy part, skip to the second line of ~~~~~.
When I was in eighth grade, there were only 40 or so kids in the entire grade. As a result, I was friends with everyone, and since that’s right around the time when guys start getting into girls, my friend was inevitably my crush as well. I’m not alone when I say that, either. This girl, we’ll change her name to Charlotte, was the first in the grade to really develop. She had grown taller faster than anyone else, and her body matched that pace. So by the time eighth grade ended, she had been the subject of many male fantasies.
Unfortunately, that school ended in eighth grade, and we all went our separate ways. Some moved into public schools, some into private schools, but rarely did more than 5 kids end up at the same school. Charlotte and I ended up at schools 20 minutes away from our middle school, but in opposite directions. Through high school, I never really saw her, except for her occasional instagram posts and Snapchat stories. But I loved seeing these posts. She was your typical partier, going to the mall at insane hours, going to friends houses until 3am on a Wednesday, going to the beach for the weekend. Of course, there was almost always alcohol or drugs or juuls present, and she did nothing to hide it. She also didn’t hide her body. In the vast majority of her posts, she wore pretty revealing clothes; showing midriff, tons of cleavage, etc. When she went to the beach it was even better. She still kept her body from when I knew her in middle school, and I loved it. Here’s when we fast forward to the event in question.
TL;DR… middle school best friend and crush had a great body, kept it throughout high school, as I saw with social media posts.
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While she had been blessed with great physical features, I was not. When I got to high school I had a shitload of acne and was about 5’6”, 210 lbs. That didn’t happen over the summer, obviously, so when I was crushing on Charlotte, there was no way she’d see me as anything but a friend. I wasn’t the most attractive guy in the grade, and I knew that. I started working out after school, and got really into hockey. I had been playing for a few years, but I started high school hockey, and I was the starting varsity goalie for my team as a freshman. When I didn’t have practice or a game, I worked out. By the end of 10th grade, I had grown to 5’10 and slimmed down to 165, all muscle. It took me two and a half years, but I also got rid of my acne. By senior year, I looked like a totally different person than I had four years prior.
I also kept up playing hockey, and this is the important part in the story. I had been playing for a team that wasn’t my own (as I was a goalie and I could do that), but that changed senior year. I began playing for my school’s team. And my school just so happened to be in the same league as the school Charlotte went to. Of course, I didn’t know that until we played them in November. I looked at the schedule and on the entire drive to the ice rink I was wondering if she was gonna be there. I drive a minivan (make fun of me now lmao) and keep that in mind for the rest of the story. So anyways, I pull up to the rink, park, get to the locker room, and get dressed. Once the referees are on the ice, we all walk out and hop on the ice. As I’m skating around, I glance up in the stands and guess who I see? I see Charlotte with a bunch of her friends. Immediately I’m trying extra hard. The game starts, blah blah goal whatever, and we win, 3-0. We shake the other teams hands, I leave the ice, get undressed, and leave the locker room.
TL;DR… I play hockey, I’m in shape, had a hockey game and Charlotte was there.
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I leave the locker room and walk out into the hallway when I see her, standing with her friends. She sees me, glances at my jacket (which says my last name on it), and then back up at me, and grins. I barely have time do drop my gear on the ground before she tackles me in a hug.
“u/quawsedc! How are you? How’s school been? You played really well, but next time let us win, okay?” She spews out sentences a mile a minute, and I have to regain my breath before I can reply. “I’m good, school’s good, and thanks, but no thanks,” I say. She smiles, drags me to her friends, and introduces me to them. The most interesting one is her boyfriend, who she’s apparently been dating for three years. Good for him. We stand talking for a while before I notice the time. “Look, I’ve got to go. It was really nice seeing you, and nice meeting all your friends,” I say. Charlotte gives me a hug, I pick up my gear, and start walking towards the exit.
I’m at my car when I hear running behind me. I turn around and see Charlotte running towards me. She comes to a stop. “I figured I’d hang out with you a while and catch up,” she says. I nod, finish putting my gear in the trunk, and close it. “Why don’t we sit in the car a while,” I suggest. She likes that idea, and she hops in the back seat. I’ve barely sat down when she hugs me again. I hug her back.
“I missed you,” she whispers. I can feel her boobs pushing against my chest, and I have to try to keep myself down. “I missed you too,” I reply. She looks up at me, seemingly analyzing my features. “You look really different than you did in middle school,” she says. “Well yeah,” I answer. “I’ve been working out every day, so I lost a lot of weight.” She shakes her head. “No, I mean you look really attractive now.” I’m stunned. “I thought you have a boyfriend?” I ask, confused as to why she’d even bring up the subject. She smiles and rolls her eyes. “I’m allowed to tell you you’re hot, even if I have a boyfriend,” she says. I shrug. “What I’m not allowed to do is this,” she whispers, and kisses me on the cheek.
She grabs my hands. I’m speechless, I have no idea what’s going on. She keeps talking. “See the thing is, my boyfriend is really bad at making me feel good… intimately. I’ve been trying to think of a guy who can help me, but I want someone who I know I have a connection with. If you’re okay with it, I’d like to give you a try.”
“I… uh… yeah, for sure,” I stutter. “What exactly do you want me to do?” I ask.
“Everything,” she says, and leans forward. Our lips meet and we immediately begin exploring each other. My hands roam all over her back and find her ass, which is beautifully shaped to be perfect for grabbing. I grab at it and pull her closer to me as her hand finds the back of my head and pulls me closer. Her other hand goes straight for my dick, which gets hard almost instantly. We keep at it for a few minutes before she pulls away.
“You’re already doing better than him,” she says. I grin and give her a quick kiss.
“I’m certainly doing my best,” I say, and flip her onto her back. I kneel on the floor, so that she’s laying on the seat and I’m next to her, and keep kissing her. My right hand snakes its way down her face, across her chest, stopping for a few grabs, of course, and then continues down her stomach. I get to her legs and start rubbing them. Every time I get close to her groin or touch her inter thigh, she flinches a little. At one point, I move my hand across her crotch from one leg to another, and she opens them invitingly. I take that as all the invitation I need. I start rubbing her through her tights, illiciting a gasp whenever I brush her clit. Slowly, I move my hand under her pants, and then under her panties. My fingers dip down to where her vagina is, and it’s soaking wet. I play around a little bit, getting my fingers nice and wet, before moving up to her clit. I find the little nub and begin gently rubbing it. As soon as I start, she gasps, stops kissing me and grabs the back of my hair. She pulls me close to her neck and I begin kissing her neck as I finger her. She moans, occasionally saying my name or cursing. It’s pretty clear that I’m doing a good job. I keep this up for a few minutes, bringing the speed up and back down, essentially edging her. Eventually, she squeezes my neck and breathily says, “stop…. teasing…. already…” I oblige. I pick up the pace and she arches her back, pushing her pussy into my fingers. I keep kissing her neck, and she orgasms. Her hand reaches down, grabs mine, and pulls it harder into her clit. Her breaths are short, and for a solid 30 seconds we stay like this, her body convulsing and twitching around my fingers. And then she goes limp. She lets go of my hand, my head, and I bring my hand out of her pants and look at her. We stare into each other’s eyes and smile.
She’s still breathing heavily. “I think I’ve found the one,” she says. We both smile and kiss again, but she pulls away. “Let’s keep going,” she says. Of course, I won’t object to that. She sits up and pulls her shirt off, exposing her bra. Then she takes that off and I can’t believe how lucky I am. As mentioned way before, she has beautiful tits. If I had to guess, probably D cup, but they don’t sag under their own weight. I sit there, kinda staring, before she says “It’s not nice to stare, and you have to take yours off too.” I didn’t really comprehend what she said, so she does it for me. She pulls off my shirt, and now it’s her turn to stare. My body’s completely changed from the last time she saw me, so now I have abs and defined pecs. I grin and playfully poke her in the boob. “It’s not nice to stare,” I laugh. She laughs too and smiles.
Without speaking, she pulls off her tights. Her panties go along for the ride. She sits up, leans against the car window, and spreads her legs, and all of a sudden, she’s completely naked in front of me. I try not to stare. I sit up on the seat and pull my own pants off. Luckily, my dick is hard from looking at her, and it jumps up to attention when I free it. Charlotte can’t help but stare.
“Too big?” I ask, grinning. She shakes her head. “Absolutely not,” she says. “It’s just that my boyfriend’s never made it to this point. I always suck him off and he cums then.” I raise my eyebrows. “So you’re a virgin?” I ask. “No,” she responds. “I’ve done it once with someone else, but they pale in comparison to you.” I smile and scoot towards her. I get on top of her and line myself up. I look at her and kiss her before saying, “well, now you’re gonna know what this should really feel like.”
I slowly push into her, inch by inch. She’s soaking wet, so it slides in easily, but she’s super tight and I need to make sure I don’t hurt her. She gasps, tilts her head back and closes her eyes. I push in until I’m balls deep inside of her. I kiss her neck and move my hand to her tits and being rolling her nipples between my fingers as I start thrusting. Slowly at first, I bring my dick almost all they way out before pushing back in. I can feel her pussy walls expanding to welcome me, and they occasionally clench in unison with her gasps and moans. I pick up the pace, still pulling all the way out and pushing in again, now with greater speed and force. Her gasps turn to moans as I speed up. She moves her right hand down to her clit and begins playing with herself. Her pussy contracts more frequently, and she experiences a sensory overload. I’m kissing her neck. I’m playing with her nipples. She’s rubbing herself. I’m fucking her. It’s too much for her, and she throws her head back and cums for the second time. Her moans get louder. I keep kissing her neck and playing with her tits. I don’t slow down my thrusts as she arches her back and throws back her head. She wraps her legs around my back and her pussy gets so tight it’s hard to push in with the same speed. But I manage. Her walls contract around my dick, trying to pull me in further. I let her, pushing in and keeping it in as she spasms beneath me.
Once she’s done, I pull out and kiss her on the lips. She’s still breathing heavily, but she manages to talk. “That was incredible. Thank you so much,” she says. I smile. “I did my best,” I reply. “Now, your boyfriend might be wondering what’s taking so long. You might want to get back.” She shakes her head. “I don’t think I need to worry about him anymore,” she says. “Besides, you haven’t cum yet!” I smile. “Thanks for worrying about me, but you don’t need to. I’ll be fine,” I say, but she laughs. “Fuck no! You’re cumming, even if I have to do it with my feet!” She exclaims. Then her smile fades. “I won’t have to do it with my feet, right?” she asks, hesitantly. Now it’s my turn to laugh. “Of course not,” I say. “I almost came inside of you right there.” She grins and says, “well let’s put you back inside of me then.” I smile but gesture at my dick, which has gone limp in the ensuing conversation. She looks at it, but doesn’t even flinch as she gets on the floor of the car, right between my knees.
She looks at me and takes it in her hand. It’s still glistening from her own juices, but she licks them off, base to head. Then she puts the whole thing in her mouth and begins tonguing it. I’m a grower, so my cock easily fit in her mouth limp, but as it grew, she had a hard time. She looks at me and starts sucking me off, doing the classic head bobbing thing as she stroked what she couldn’t fit in her mouth. I moan and say, “god, I can see how your boyfriend doesn’t last long when you do this.” At this, she stops, stands up, and straddles me. She positions my tip at her pussy and looks me dead in the eyes. “EX- boyfriend,” she corrects, and falls on my dick.
Surprisingly, shes able to take my entire length at once, and man does it feel good. She’s super tight, and as she bounces up and down, I can enjoy the same feeling as before without having to do any work. I grab her ass and help her move, occasionally alternating between bouncing and grinding. Her tits are right in my face, so I use one hand to stabilize one and start sucking on her nipple. She loves it, and starts moaning. She moves one hand down to her clit and starts rubbing it, and the grinding stops. We keep at it for a minute or so, her bouncing up and down on my cock, me sucking on her nipples, and her playing with herself. Soon enough, I can feel her pussy tighten. She gasps and I move both of my hands to her ass. Just like before, her pussy gets so tight, tighter than before. She keeps bouncing on me. “Charlotte… I’m cumming…” I say between breaths, and she grins. She stops bouncing and starts grinding on me in a circular pattern as her pussy contracts. I grab her ass and push in as far as I can go, releasing my cum deep inside of her. With each spurt, I try to pull as far into her as I can. Her pussy milks my cum out of me until every last drop has been deposited inside her womb. She sits on top of me and leans down. She pulls my head up for a long kiss and then says “I’m so happy we did this. I love you.” I smile and playfully slap her ass. “I love you too,” I say.
We smile at each other and kiss again, this time kissing for minutes before we pull apart. She’s still on top of me, and occasional pussy squeezes have kept me from going totally limp. She slowly pulls me out, and to my surprise, nothing drips out. She looks down and digs around for a second before downing me her fingers. “Nothing,” she says, and licks her fingers clean. “You must’ve gotten yourself way up there.”
“Good,” I say. “That means you’re mine.” She smiles. We both get dressed, with occasional kissing, and she goes back inside to meet her friends.
We started dating after that, and we have been for just about a year at this point. We both ended up at the state university, so we keep at it there. Fucking and sucking, very often, and I have no plans to break up with her anytime soon. I just have to hope she finds our sex satisfying, otherwise she might go try to find another guy, and I’ll be on the receiving end this time…

Source: reddit.com/r/gonewildstories/comments/a24wce/creaming_my_best_friend_and_crush_from_5_years